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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Uncovering the Importance of Proton Donors in TmI<sub>2</sub>-Promoted Electron Transfer: Facile C−N Bond Cleavage in Unactivated Amides<xref ref-type="author-notes" rid="fn1">**</xref></title><author><name sortKey="Szostak, Michal" sort="Szostak, Michal" uniqKey="Szostak M" first="Michal" last="Szostak">Michal Szostak</name></author><author><name sortKey="Spain, Malcolm" sort="Spain, Malcolm" uniqKey="Spain M" first="Malcolm" last="Spain">Malcolm Spain</name></author><author><name sortKey="Procter, David J" sort="Procter, David J" uniqKey="Procter D" first="David J" last="Procter">David J. Procter</name></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">23828793</idno><idno type="pmc">4265963</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4265963</idno><idno type="RBID">PMC:4265963</idno><idno type="doi">10.1002/anie.201303178</idno><date when="2013">2013</date><idno type="wicri:Area/Pmc/Corpus">000353</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000353</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Uncovering the Importance of Proton Donors in TmI<sub>2</sub>-Promoted Electron Transfer: Facile C−N Bond Cleavage in Unactivated Amides<xref ref-type="author-notes" rid="fn1">**</xref></title><author><name sortKey="Szostak, Michal" sort="Szostak, Michal" uniqKey="Szostak M" first="Michal" last="Szostak">Michal Szostak</name></author><author><name sortKey="Spain, Malcolm" sort="Spain, Malcolm" uniqKey="Spain M" first="Malcolm" last="Spain">Malcolm Spain</name></author><author><name sortKey="Procter, David J" sort="Procter, David J" uniqKey="Procter D" first="David J" last="Procter">David J. Procter</name></author></analytic><series><title level="j">Angewandte Chemie (International Ed. in English)</title><idno type="ISSN">1433-7851</idno><idno type="eISSN">1521-3773</idno><imprint><date when="2013">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Greenberg, A" uniqKey="Greenberg A">A Greenberg</name></author><author><name sortKey="Breneman, Cm" uniqKey="Breneman C">CM Breneman</name></author><author><name sortKey="Liebman, Jf" uniqKey="Liebman J">JF Liebman</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Nahm, S" uniqKey="Nahm S">S Nahm</name></author><author><name sortKey="Weinreb, Sm" uniqKey="Weinreb S">SM Weinreb</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Balasubramaniam, S" uniqKey="Balasubramaniam S">S 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Angew Chem Int Ed Engl</journal-id><journal-id journal-id-type="iso-abbrev">Angew. Chem. Int. Ed. Engl</journal-id><journal-id journal-id-type="publisher-id">anie</journal-id><journal-title-group><journal-title>Angewandte Chemie (International Ed. in English)</journal-title></journal-title-group><issn pub-type="ppub">1433-7851</issn><issn pub-type="epub">1521-3773</issn><publisher><publisher-name>WILEY-VCH Verlag</publisher-name><publisher-loc>Weinheim</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">23828793</article-id><article-id pub-id-type="pmc">4265963</article-id><article-id pub-id-type="doi">10.1002/anie.201303178</article-id><article-categories><subj-group subj-group-type="heading"><subject>Communications</subject></subj-group></article-categories><title-group><article-title>Uncovering the Importance of Proton Donors in TmI<sub>2</sub>-Promoted Electron Transfer: Facile C−N Bond Cleavage in Unactivated Amides<xref ref-type="author-notes" rid="fn1">**</xref></article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Szostak</surname><given-names>Michal</given-names></name><role>Dr.</role><xref ref-type="corresp" rid="cor1">*</xref></contrib><contrib contrib-type="author"><name><surname>Spain</surname><given-names>Malcolm</given-names></name></contrib><contrib contrib-type="author"><name><surname>Procter</surname><given-names>David J</given-names></name><role>Prof. Dr.</role><xref ref-type="corresp" rid="cor2">*</xref></contrib><aff><institution>School of Chemistry, University of Manchester</institution><addr-line>Oxford Road, Manchester M13 9PL (UK)</addr-line></aff></contrib-group><author-notes><corresp id="cor1">*E-mail: <email>michal.szostak@manchester.ac.uk</email></corresp><corresp id="cor2">*E-mail: <email>david.j.procter@manchester.ac.uk</email></corresp><fn><p>Homepage: <ext-link ext-link-type="uri" xlink:href="http://people.man.ac.uk/~mbdssdp2/">http://people.man.ac.uk/~mbdssdp2/</ext-link></p></fn><fn id="fn1"><label>**</label><p>We acknowledge the EPSRC and GSK for financial support.</p></fn></author-notes><pub-date pub-type="ppub"><day>08</day><month>7</month><year>2013</year></pub-date><pub-date pub-type="epub"><day>12</day><month>6</month><year>2013</year></pub-date><volume>52</volume><issue>28</issue><fpage>7237</fpage><lpage>7241</lpage><history><date date-type="received"><day>16</day><month>4</month><year>2013</year></date></history><permissions><copyright-statement>© 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</copyright-statement><copyright-year>2013</copyright-year><license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/3.0/"><license-p>This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</license-p></license></permissions><kwd-group><kwd>amides</kwd><kwd>C−N cleavage</kwd><kwd>electron transfer</kwd><kwd>lanthanides</kwd><kwd>thulium diiodide</kwd></kwd-group></article-meta></front><body><p>The amide bond is one of the most ubiquitious functional groups in chemistry and biology.<xref rid="b1" ref-type="bibr">1</xref> To date, the majority of strategies to functionalize amide bonds have focused on activation of the carbonyl group towards nucleophilic addition,<xref rid="b2a" ref-type="bibr">2</xref> however only few examples of the selective activation of σ C–N bonds in amides have been reported. In this regard, the cleavage of a σ C−N bond in amides was achieved in several highly innovative but very specialized bridged lactams, in which one of the C−N bonds was sufficiently distorted from planarity (Figure <xref ref-type="fig" rid="fig01">1 a</xref>).<xref rid="b3a" ref-type="bibr">3</xref> Functionalization of the C−N bond in electronically activated phthalimides has also been described.<xref rid="b4a" ref-type="bibr">4</xref> However, a general method for the activation of σ C−N bonds in amides is unknown despite its considerable potential to advance the synthetic application of amide linkages in chemistry and biology.</p><fig id="fig01" position="float"><label>Figure 1</label><caption><p>a) Cleavage of unactivated σ C−N bonds in amides. b) Classical and nonclassical lanthanide(II) iodides. c) This study.</p></caption><graphic xlink:href="anie0052-7237-f1"></graphic></fig><p>The discovery of new reactivity modes of underexplored elements underpins major advancements in synthesis. In this regard, the seminal discovery of Kagan and co-workers that SmI<sub>2</sub> acts as a strong electron donor<xref rid="b5a" ref-type="bibr">5</xref> has resulted in one of the most important single-electron transfer reagents in organic chemistry.<xref rid="b6" ref-type="bibr">6</xref>, <xref rid="b7a" ref-type="bibr">7</xref> However, the inherent limitation of SmI<sub>2</sub> is its relatively low redox potential (<italic>E</italic>° (Ln<sup>III/II</sup>)=−1.5 V vs. NHE),<xref rid="b8" ref-type="bibr">8</xref> especially when compared with the extremely powerful, albeit less chemoselective, alkali metals in liquid ammonia (i.e. Birch-type reductants).<xref rid="b9a" ref-type="bibr">9</xref> Recently, nonclassical lanthanide(II) iodides (TmI<sub>2</sub>, thulium diiodide; DyI<sub>2</sub>, dysprosium diiodide; NdI<sub>2</sub>, neodymium diiodide) have emerged as an attractive solution to the problem of insufficient redox potential of SmI<sub>2</sub> (Figure <xref ref-type="fig" rid="fig01">1 b</xref>).<xref rid="b10a" ref-type="bibr">10</xref> In analogy to SmI<sub>2</sub>, these extremely reducing lanthanide iodides (<italic>E</italic>° (Ln<sup>III/II</sup>)=−2.2, −2.5, −2.6 V vs. NHE,<xref rid="b8" ref-type="bibr">8</xref> respectively) have been fully characterized in ethereal solvents<xref rid="b11a" ref-type="bibr">11</xref> and can be easily obtained in multigram quantities.<xref rid="b12a" ref-type="bibr">12</xref> Seminal work by Evans et al. provided the first evidence that TmI<sub>2</sub>, DyI<sub>2</sub>, and NdI<sub>2</sub> mediate challenging cross-coupling reactions beyond the scope of SmI<sub>2</sub>.<xref rid="b13a" ref-type="bibr">13</xref> Evans et al. also reported DyI<sub>2</sub> as the first lanthanide(II) reagent capable of promoting Birch reductions under very mild conditions.<xref rid="b11b" ref-type="bibr">11b</xref> However, the direct use of nonclassical lanthanides(II) to generate ketyl radicals has not been reported despite their significant potential to activate C—O groups that are typically resistant to open-shell reaction pathways.</p><p>Herein, we demonstrate that the TmI<sub>2</sub>−ROH reagent (R=H, Me), formed from the first nonclassical lanthanide(II) iodide in the series, promotes a highly unusual cleavage of the σ C−N bond in planar amides. Moreover, we report that TmI<sub>2</sub>−ROH is the first lanthanide(II) reagent to selectively generate ketyl radicals from aliphatic esters. Finally, we demonstrate that the presence of alcohols is critical for the formation of thermodynamically more powerful reductants from TmI<sub>2</sub> (TmI<sub>2</sub>(ROH)<sub><italic>n</italic></sub>, <italic>E</italic>°=−2.6 V vs. SCE).</p><p>We recently developed approaches for the chemoselective reduction of cyclic esters<xref rid="b14a" ref-type="bibr">14a</xref> and 1,3-diesters<xref rid="b14b" ref-type="bibr">14b</xref> by using a SmI<sub>2</sub>−H<sub>2</sub>O reagent. These reactions were the first examples of the activation of carbonyls that are traditionally unreactive towards SmI<sub>2</sub>. On the basis of these results, we initiated efforts to chemoselectively activate other types of carbonyl by using lanthanide(II) reagents. We hypothesized that the use of the more-reducing nonclassical lanthanide(II) iodides would result in a chemoselective generation of acyl-type radicals from carboxylic acid derivatives that lie beyond the scope of SmI<sub>2</sub>. In particular, we considered that highly reducing nonclassical lanthanide(II) iodides that are additionally activated by proton donors, could potentially permit productive electron transfer to amide carbonyls, a functional group that has been traditionally resistant to single-electron-transfer reductants, as a result of n<sub>N</sub>→π*<sub>C—O</sub> conjugation.<xref rid="b1" ref-type="bibr">1</xref> With these considerations in mind, we subjected <italic>N</italic>,<italic>N</italic>-dialkyl amide <bold>1 a</bold> to several TmI<sub>2</sub>-mediated reaction conditions (Table <xref ref-type="table" rid="tbl1">1</xref>). To our delight, with MeOH as the proton source, we observed efficient formation of <italic>N</italic>-monoalkyl amide <bold>2 a</bold>, in which a highly unusual cleavage of the σ C−N bond took place (Table <xref ref-type="table" rid="tbl1">1</xref>, entry 3; see the Supporting Information for reagent stability studies). Control reactions demonstrated that the reaction did not proceed in the absence of a proton source (Table <xref ref-type="table" rid="tbl1">1</xref>, entry 1), at low concentration of MeOH (Table <xref ref-type="table" rid="tbl1">1</xref>, entry 2), with H<sub>2</sub>O as an alternative additive (Table <xref ref-type="table" rid="tbl1">1</xref>, entry 5), and with a variety of SmI<sub>2</sub> systems (Table <xref ref-type="table" rid="tbl1">1</xref>, entries 6–8; see also the Supporting Information). Furthermore, the corresponding aliphatic pyrrolidinyl amine was inert to the reaction conditions (Table <xref ref-type="table" rid="tbl1">1</xref>, entry 4), thus demonstrating high levels of chemoselectivity imparted by the TmI<sub>2</sub> reagent.<xref rid="b15a" ref-type="bibr">15</xref></p><table-wrap id="tbl1" position="float"><label>Table 1</label><caption><p>Optimization of the C−N bond cleavage in unactivated amides in the presence of LnI<sub>2</sub>(ROH)<sub><italic>n</italic></sub>.</p></caption><table frame="hsides" rules="groups"><thead><tr><th colspan="7" rowspan="1"><graphic xlink:href="anie0052-7237-g1"></graphic></th></tr><tr><th align="left" rowspan="1" colspan="1">Entry</th><th align="left" rowspan="1" colspan="1">LnI<sub>2</sub></th><th align="left" rowspan="1" colspan="1">LnI<sub>2</sub> (equiv)</th><th align="left" rowspan="1" colspan="1">ROH</th><th align="left" rowspan="1" colspan="1">ROH (equiv)<xref ref-type="table-fn" rid="tf1-1">[a]</xref></th><th align="left" rowspan="1" colspan="1"><italic>t</italic><xref ref-type="table-fn" rid="tf1-2">[b]</xref></th><th align="left" rowspan="1" colspan="1">Yield [%]<xref ref-type="table-fn" rid="tf1-3">[c]</xref></th></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1">1</td><td align="left" rowspan="1" colspan="1">TmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">2 h</td><td align="left" rowspan="1" colspan="1"><2</td></tr><tr><td align="left" rowspan="1" colspan="1">2</td><td align="left" rowspan="1" colspan="1">TmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">10</td><td align="left" rowspan="1" colspan="1">3 min</td><td align="left" rowspan="1" colspan="1"><2</td></tr><tr><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">TmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">100</td><td align="left" rowspan="1" colspan="1">3 min</td><td align="left" rowspan="1" colspan="1">48 (77)<xref ref-type="table-fn" rid="tf1-4">[d]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">4<xref ref-type="table-fn" rid="tf1-5">[e]</xref></td><td align="left" rowspan="1" colspan="1">TmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">100</td><td align="left" rowspan="1" colspan="1">3 min</td><td align="left" rowspan="1" colspan="1"><2</td></tr><tr><td align="left" rowspan="1" colspan="1">5</td><td align="left" rowspan="1" colspan="1">TmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">H<sub>2</sub>O</td><td align="left" rowspan="1" colspan="1">150</td><td align="left" rowspan="1" colspan="1">3 min</td><td align="left" rowspan="1" colspan="1"><2</td></tr><tr><td align="left" rowspan="1" colspan="1">6<xref ref-type="table-fn" rid="tf1-6">[f]</xref></td><td align="left" rowspan="1" colspan="1">SmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">3 h</td><td align="left" rowspan="1" colspan="1"><2</td></tr><tr><td align="left" rowspan="1" colspan="1">7<xref ref-type="table-fn" rid="tf1-6">[f]</xref></td><td align="left" rowspan="1" colspan="1">SmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">100</td><td align="left" rowspan="1" colspan="1">3 h</td><td align="left" rowspan="1" colspan="1"><2</td></tr><tr><td align="left" rowspan="1" colspan="1">8<xref ref-type="table-fn" rid="tf1-6">[f]</xref></td><td align="left" rowspan="1" colspan="1">SmI<sub>2</sub></td><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">H<sub>2</sub>O</td><td align="left" rowspan="1" colspan="1">100</td><td align="left" rowspan="1" colspan="1">1 h</td><td align="left" rowspan="1" colspan="1"><2</td></tr></tbody></table><table-wrap-foot><fn id="tf1-1"><label>[a]</label><p>With respect to LnI<sub>2</sub>.</p></fn><fn id="tf1-2"><label>[b]</label><p>Time elapsed until characteristic color change from Tm<sup>II</sup> to Tm<sup>III</sup>.</p></fn><fn id="tf1-3"><label>[c]</label><p>Determined by <sup>1</sup>H NMR spectroscopy and/or GC–MS.</p></fn><fn id="tf1-4"><label>[d]</label><p>In parentheses, yield based on the recovered starting material. TmI<sub>2</sub> (6 equiv) afforded <bold>2 a</bold> in 45 % yield.</p></fn><fn id="tf1-5"><label>[e]</label><p>The corresponding amine was used instead of the amide.</p></fn><fn id="tf1-6"><label>[f]</label><p>Azetidinyl amide <bold>1 d</bold> used instead of the pyrrolidinyl amide. Reaction conditions: LnI<sub>2</sub> (3 equiv), ROH (H<sub>2</sub>O, 150 equiv; MeOH, 100 equiv), THF, 23 °C. See the Supporting Information for details.</p></fn></table-wrap-foot></table-wrap><p>With the optimized conditions in hand, a series of amides was subjected to the reaction to provide an initial examination of the scope of this transformation (Scheme <xref ref-type="fig" rid="fig02">1</xref>). The C−N bond scission occurred for both unhindered and sterically encumbered pyrrolidinyl amides (<bold>1 a</bold>–<bold>1 c</bold>). Moreover, the reaction of the azetidinyl amide <bold>1 d</bold> demonstrated that the reaction is applicable to other cyclic amides. In addition, two acyclic amides (<bold>1 e</bold>–<bold>1 f</bold>) were similarly cleaved, thus demonstrating that the cyclic structure of amides is not necessary for the scission. Importantly, secondary <italic>n</italic>-alkyl and <italic>n</italic>-aryl amides did not undergo the cleavage reaction (see the Supporting Information), thus indicating complete selectivity of the reducing system for these tertiary amides. To gain a preliminary mechanistic insight, we subjected a sterically biased aziridinyl amide <bold>1 g</bold> to the reaction conditions. The reaction afforded an approximately 1.6:1.0 ratio of regioisomeric amides, with the predominant product resulting from cleavage at the less substituted carbon center. On the basis of this experiment and the known propensity of nonclassical LnI<sub>2</sub> to cleave C−O bonds in ethers,<xref rid="b15a" ref-type="bibr">15</xref> we propose that the mechanism of the TmI<sub>2</sub>-mediated cleavage involves a direct insertion of Tm<sup>II</sup> into the C−N amide bond; however, a mechanism involving fragmentation of an initially-formed ketyl-type radical seems also to be operating in some cases as suggested by the correlation of the reaction efficiency with thermochemical stabilization energies (SE) of the fragmenting radical in the series: <italic>t</italic>Bu (71 %, SE=4.35 kcal mol<sup>−1</sup>)><italic>i</italic>Pr (29 %, SE=2.57 kcal mol<sup>−1</sup>)>Me (<2 %, SE=−1.65 kcal mol<sup>−1</sup>).<xref rid="b16" ref-type="bibr">16</xref></p><fig id="fig02" position="float"><label>Scheme 1</label><caption><p>Cleavage of unactivated σ C−N bonds in amides in the presence of TmI<sub>2</sub>(ROH)<sub><italic>n</italic></sub> at 23 °C.</p></caption><graphic xlink:href="anie0052-7237-f2"></graphic></fig><p>The mechanistic implications of the C−N cleavage merit further discussion. The present reaction with TmI<sub>2</sub> represents the first case of a general scission of unactivated σ C−N bonds in planar amides, and compares favorably with the previous examples of the cleavage of a σ C−N bond in distorted lactams<xref rid="b3a" ref-type="bibr">3</xref> (reagent vs. substrate control). Moreover, it strongly suggests that the reactivity of nonclassical lanthanides(II) extends beyond being the reagents that simply close the energy gap between SmI<sub>2</sub> and the Birch-type reductants.<xref rid="b11a" ref-type="bibr">11</xref>, <xref rid="b13a" ref-type="bibr">13a</xref></p><p>Having established that TmI<sub>2</sub>−ROH is capable of an efficient electron transfer to the amide carbonyl group but not their reduction, the reagent system was applied to the generation of ketyl radicals from esters (Table <xref ref-type="table" rid="tbl2">2</xref>). In previous work, we reported the reduction of lactones in the presence of SmI<sub>2</sub>−H<sub>2</sub>O;<xref rid="b14a" ref-type="bibr">14a</xref> however, this reaction suffered from long reaction times, was limited to unhindered substrates, and could be applied only to six-membered lactones; other ring systems and acyclic esters were unreactive under the reaction conditions. In sharp contrast, TmI<sub>2</sub>−ROH reacted with a wide range of substrates, including lactones (Table <xref ref-type="table" rid="tbl2">2</xref>, entry 1), aliphatic (Table <xref ref-type="table" rid="tbl2">2</xref>, entries 2 and 3), aromatic (Table <xref ref-type="table" rid="tbl2">2</xref>, entries 3 and 4), alpha-substituted (Table <xref ref-type="table" rid="tbl2">2</xref>, entries 4–6), and sterically demanding (Table <xref ref-type="table" rid="tbl2">2</xref>, entry 7) esters. In all cases rapid (within 2–3 min) reduction to the corresponding alcohols took place, clearly demonstrating the higher reactivity of TmI<sub>2</sub>−ROH. Control reactions established that, in the absence of proton donors, TmI<sub>2</sub> does not reduce aliphatic esters. Acids are not reduced under the reaction conditions (Table <xref ref-type="table" rid="tbl2">2</xref>, entry 8), thus opening the door for highly chemoselective reductions of carboxylic acid derivatives through single-electron reaction pathways that are not possible with the traditional alkali or transition metal hydrides.<xref rid="b9a" ref-type="bibr">9</xref> Overall, this study outlines the reactivity scale for the generation of ketyl-type radicals with TmI<sub>2</sub>−ROH (see the Supporting Information for comparison tables between TmI<sub>2</sub> and SmI<sub>2</sub>), demonstrates that useful levels of chemoselectivity are possible with TmI<sub>2</sub>−ROH, and opens the door for the use of TmI<sub>2</sub>-generated ketyls in radical bond-forming reactions.</p><table-wrap id="tbl2" position="float"><label>Table 2</label><caption><p>Reduction of aliphatic esters in the presence of TmI<sub>2</sub>(ROH)<sub><italic>n</italic></sub> at 23 °C.<sup>[a]</sup></p></caption><table frame="hsides" rules="groups"><thead><tr><th align="left" rowspan="1" colspan="1">Entry</th><th align="left" rowspan="1" colspan="1">Ester/Acid</th><th align="left" rowspan="1" colspan="1">ROH</th><th align="left" rowspan="1" colspan="1"><italic>t</italic> [min]<xref ref-type="table-fn" rid="tf2-1">[a]</xref></th><th align="left" rowspan="1" colspan="1">Yield [%]<xref ref-type="table-fn" rid="tf2-2">[b]</xref></th></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1">1</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g2"></graphic></td><td align="left" rowspan="1" colspan="1">H<sub>2</sub>O</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1">88</td></tr><tr><td align="left" rowspan="1" colspan="1">2</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g3"></graphic></td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1">99</td></tr><tr><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g4"></graphic></td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1">96</td></tr><tr><td align="left" rowspan="1" colspan="1">4</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g5"></graphic></td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1">85</td></tr><tr><td align="left" rowspan="1" colspan="1">5</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g6"></graphic></td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1">94</td></tr><tr><td align="left" rowspan="1" colspan="1">6</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g7"></graphic></td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1">63</td></tr><tr><td align="left" rowspan="1" colspan="1">7</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g8"></graphic></td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1">58</td></tr><tr><td align="left" rowspan="1" colspan="1">8</td><td align="left" rowspan="1" colspan="1"><graphic xlink:href="anie0052-7237-g9"></graphic></td><td align="left" rowspan="1" colspan="1">MeOH</td><td align="left" rowspan="1" colspan="1">2–3</td><td align="left" rowspan="1" colspan="1"><5<xref ref-type="table-fn" rid="tf2-3">[c]</xref></td></tr></tbody></table><table-wrap-foot><fn id="tf2-1"><label>[a]</label><p>Time elapsed until characteristic color change from Tm<sup>II</sup> to Tm<sup>III</sup>.</p></fn><fn id="tf2-2"><label>[b]</label><p>Determined by <sup>1</sup>H NMR spectropscopy.</p></fn><fn id="tf2-3"><label>[c]</label><p>Decanoic acid recovered in >95 %. Reaction conditions: TmI<sub>2</sub> (6–8 equiv), ROH (H<sub>2</sub>O, 150 equiv; MeOH, 100 equiv), THF, 23 °C. See the Supporting Information for details.</p></fn></table-wrap-foot></table-wrap><p>To gain a preliminary mechanistic insight into the key effect of protic additives on the properties of the TmI<sub>2</sub> reagent (note that in both cases no reaction was observed with TmI<sub>2</sub> alone, see the Supporting Information), we examined the reactivity of TmI<sub>2</sub> with a set of aromatic hydrocarbons with gradually increasing redox potentials in the presence of MeOH (Table <xref ref-type="table" rid="tbl3">3</xref>).<xref rid="b17" ref-type="bibr">17</xref> In this study, the TmI<sub>2</sub>−MeOH complex was found to reduce aromatic hydrocarbons with redox potentials up to −2.6 V (vs. SCE); however, benzene was inert under the reaction conditions. These results suggest that the addition of MeOH to TmI<sub>2</sub> results in an increase of the reduction potential of TmI<sub>2</sub> by approximately 0.6 V.<xref rid="b13d" ref-type="bibr">13d</xref></p><table-wrap id="tbl3" position="float"><label>Table 3</label><caption><p>Determination of the redox potential of TmI<sub>2</sub>(ROH)<sub><italic>n</italic></sub> by reduction of aromatic hydrocarbons.</p></caption><table frame="hsides" rules="groups"><thead><tr><th align="left" rowspan="1" colspan="1">Entry</th><th align="left" rowspan="1" colspan="1">Hydrocarbon</th><th align="left" rowspan="1" colspan="1">−<italic>E</italic><sub>1/2</sub> [V]<xref ref-type="table-fn" rid="tf3-1">[a]</xref></th><th align="left" rowspan="1" colspan="1">Reaction with TmI<sub>2</sub> observed<xref ref-type="table-fn" rid="tf3-3">[c]</xref></th></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1">1</td><td align="left" rowspan="1" colspan="1">cyclooctatetraene<xref ref-type="table-fn" rid="tf3-2">[b]</xref></td><td align="left" rowspan="1" colspan="1">1.83</td><td align="left" rowspan="1" colspan="1">+</td></tr><tr><td align="left" rowspan="1" colspan="1">2</td><td align="left" rowspan="1" colspan="1">anthracene</td><td align="left" rowspan="1" colspan="1">1.98</td><td align="left" rowspan="1" colspan="1">+</td></tr><tr><td align="left" rowspan="1" colspan="1">3</td><td align="left" rowspan="1" colspan="1">stilbene</td><td align="left" rowspan="1" colspan="1">2.21</td><td align="left" rowspan="1" colspan="1">+</td></tr><tr><td align="left" rowspan="1" colspan="1">4</td><td align="left" rowspan="1" colspan="1">1,4-diphenylbenzene</td><td align="left" rowspan="1" colspan="1">2.40</td><td align="left" rowspan="1" colspan="1">+</td></tr><tr><td align="left" rowspan="1" colspan="1">5</td><td align="left" rowspan="1" colspan="1">1,3,5-triphenylbenzene</td><td align="left" rowspan="1" colspan="1">2.51</td><td align="left" rowspan="1" colspan="1">+</td></tr><tr><td align="left" rowspan="1" colspan="1">6</td><td align="left" rowspan="1" colspan="1">naphthalene</td><td align="left" rowspan="1" colspan="1">2.61</td><td align="left" rowspan="1" colspan="1">+</td></tr><tr><td align="left" rowspan="1" colspan="1">7</td><td align="left" rowspan="1" colspan="1">styrene</td><td align="left" rowspan="1" colspan="1">2.65</td><td align="left" rowspan="1" colspan="1">+</td></tr><tr><td align="left" rowspan="1" colspan="1">8</td><td align="left" rowspan="1" colspan="1">benzene</td><td align="left" rowspan="1" colspan="1">3.42</td><td align="left" rowspan="1" colspan="1">−</td></tr></tbody></table><table-wrap-foot><fn id="tf3-1"><label>[a]</label><p>In volts vs. SCE; <italic>E</italic><sub>1/2</sub> describes half-reduction potential; see Ref. <xref rid="b17" ref-type="bibr">17</xref>.</p></fn><fn id="tf3-2"><label>[b]</label><p>Ref. <xref rid="b13d" ref-type="bibr">13d</xref>.</p></fn><fn id="tf3-3"><label>[c]</label><p>Determined by GC and/or <sup>1</sup>H NMR spectroscopy.</p></fn></table-wrap-foot></table-wrap><p>Furthermore, deuterium incorporation and kinetic isotope effect studies in the reduction of stilbene, a reaction that is known to proceed through an outer-sphere electron-transfer mechanism,<xref rid="b18" ref-type="bibr">18</xref> using TmI<sub>2</sub>−ROH ([D<sub>4</sub>]methanol, 96.5 % D<sub>2</sub> incorporation, <italic>k</italic><sub>H</sub>/k<sub>D</sub>=1.13±0.1; D<sub>2</sub>O, 98.0 % D<sub>2</sub> incorporation, <italic>k</italic><sub>H</sub>/k<sub>D</sub>=1.27±0.1), suggest that the increase in reduction potential of the reagent results from complexation between the proton donor and TmI<sub>2</sub>.</p><p>A detailed examination of different proton donors in the model system (see the Supporting Information) revealed that a much lower concentration of alcohols (10 equiv) is required to enhance the redox potential of TmI<sub>2</sub> in comparison with SmI<sub>2</sub> (100 equiv).<xref rid="b19a" ref-type="bibr">19</xref> This result is consistent with the smaller radial size of Tm<sup>II</sup> and bodes well for the development of catalytic cycles based on regeneration of the TmI<sub>2</sub> reagent.<xref rid="b20" ref-type="bibr">20</xref></p><p>Finally, to test whether in analogy to amides a bond cleavage mechanism also contributes to the reduction of esters with TmI<sub>2</sub>, we subjected decyl and 1-phenylethyl acetate to the reaction conditions (Scheme <xref ref-type="fig" rid="fig03">2</xref>). C−O bond scission was the minor pathway in the case of <bold>3</bold> and the predominant one in the case of <bold>4</bold>; these results indicate that the cleavage is also operating in the ester reduction and provides a unifying reactivity model for the TmI<sub>2</sub>-mediated electron transfer.<xref rid="b13a" ref-type="bibr">13a</xref></p><fig id="fig03" position="float"><label>Scheme 2</label><caption><p>Investigating the mechanism of ester reduction with TmI<sub>2</sub>(ROH)<sub><italic>n</italic></sub>.</p></caption><graphic xlink:href="anie0052-7237-f3"></graphic></fig><p>In summary, the highly unusual cleavage of unactivated σ C−N bonds in amides in the presence of TmI<sub>2</sub>, the first nonclassical lanthanide(II) iodide in the series (TmI<sub>2</sub>, DyI<sub>2</sub>, NdI<sub>2</sub>), has been achieved. 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