Complex‐Induced Proximity Effect in the Regioselective Lithiation of Pyridine Derivatives
Identifieur interne : 000313 ( Istex/Curation ); précédent : 000312; suivant : 000314Complex‐Induced Proximity Effect in the Regioselective Lithiation of Pyridine Derivatives
Auteurs : Jaspreet S. Dhau [Inde] ; Amritpal Singh ; Yoganjaneyulu Kasetti [Inde] ; P. V. Bharatam [Inde]Source :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2012-03.
English descriptors
- KwdEn :
- Adduct, Calcd, Cdcl3, Chem, Cipe, Complexation, Deprotonation, Derivative, Diethyl, Diethyl ether, Dilithiation, Electrophile, Electrostatic effect, Elemental selenium, Equiv, Ether, Gmbh, Gros, Inert atmosphere, Kgaa, Lithiation, Lithium, Ltmp, Methyl, Methyl carbon, Mmol, Proximity effect, Pyridine, Pyridine derivatives, Reaction mixture, Regioselective, Regioselective lithiation, Regioselective ring lithiation, Relative stability, Ring lithiation, Room temperature, Sch3 sech3, Sech3, Selenium, Singh, Verlag, Verlag gmbh, Weinheim.
- Teeft :
- Adduct, Calcd, Cdcl3, Chem, Cipe, Complexation, Deprotonation, Derivative, Diethyl, Diethyl ether, Dilithiation, Electrophile, Electrostatic effect, Elemental selenium, Equiv, Ether, Gmbh, Gros, Inert atmosphere, Kgaa, Lithiation, Lithium, Ltmp, Methyl, Methyl carbon, Mmol, Proximity effect, Pyridine, Pyridine derivatives, Reaction mixture, Regioselective, Regioselective lithiation, Regioselective ring lithiation, Relative stability, Ring lithiation, Room temperature, Sch3 sech3, Sech3, Selenium, Singh, Verlag, Verlag gmbh, Weinheim.
Abstract
The regioselective ring lithiation of BF3‐complexed 3‐picoline (1a), 3,4‐lutidine (1b), and 3,5‐lutidine (1c) was studied. The dilithiation of 1a, 1b, and 1c was also investigated to experimentally explore the relative preference of the sites on the substituted pyridine ring for lithiation. The role of the complex‐induced proximity effect (CIPE) for inducing lithiation in these moieties was investigated using both experimental and computational studies.
Url:
DOI: 10.1002/ejoc.201101592
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Amritpal Singh<affiliation><mods:affiliation>Department of Chemistry, Punjabi University, Patiala 147002, India, Fax: +91‐175‐2286682</mods:affiliation><wicri:noCountry code="subField">+91‐175‐2286682</wicri:noCountry></affiliation>Le document en format XML
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A. S., Nagar 160062, Punjab, India</mods:affiliation><country xml:lang="fr">Inde</country><wicri:regionArea>Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector‐67, S. A. S., Nagar 160062, Punjab</wicri:regionArea></affiliation></author><author><name sortKey="Bharatam, P V" sort="Bharatam, P V" uniqKey="Bharatam P" first="P. V." last="Bharatam">P. V. Bharatam</name><affiliation wicri:level="1"><mods:affiliation>Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector‐67, S. A. S., Nagar 160062, Punjab, India</mods:affiliation><country xml:lang="fr">Inde</country><wicri:regionArea>Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector‐67, S. A. S., Nagar 160062, Punjab</wicri:regionArea></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">European Journal of Organic Chemistry</title><title level="j" type="alt">EUROPEAN JOURNAL OF ORGANIC CHEMISTRY</title><idno type="ISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><imprint><biblScope unit="vol">2012</biblScope><biblScope unit="issue">9</biblScope><biblScope unit="page" from="1746">1746</biblScope><biblScope unit="page" to="1752">1752</biblScope><biblScope unit="page-count">7</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2012-03">2012-03</date></imprint><idno type="ISSN">1434-193X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1434-193X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Adduct</term><term>Calcd</term><term>Cdcl3</term><term>Chem</term><term>Cipe</term><term>Complexation</term><term>Deprotonation</term><term>Derivative</term><term>Diethyl</term><term>Diethyl ether</term><term>Dilithiation</term><term>Electrophile</term><term>Electrostatic effect</term><term>Elemental selenium</term><term>Equiv</term><term>Ether</term><term>Gmbh</term><term>Gros</term><term>Inert atmosphere</term><term>Kgaa</term><term>Lithiation</term><term>Lithium</term><term>Ltmp</term><term>Methyl</term><term>Methyl carbon</term><term>Mmol</term><term>Proximity effect</term><term>Pyridine</term><term>Pyridine derivatives</term><term>Reaction mixture</term><term>Regioselective</term><term>Regioselective lithiation</term><term>Regioselective ring lithiation</term><term>Relative stability</term><term>Ring lithiation</term><term>Room temperature</term><term>Sch3 sech3</term><term>Sech3</term><term>Selenium</term><term>Singh</term><term>Verlag</term><term>Verlag gmbh</term><term>Weinheim</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Adduct</term><term>Calcd</term><term>Cdcl3</term><term>Chem</term><term>Cipe</term><term>Complexation</term><term>Deprotonation</term><term>Derivative</term><term>Diethyl</term><term>Diethyl ether</term><term>Dilithiation</term><term>Electrophile</term><term>Electrostatic effect</term><term>Elemental selenium</term><term>Equiv</term><term>Ether</term><term>Gmbh</term><term>Gros</term><term>Inert atmosphere</term><term>Kgaa</term><term>Lithiation</term><term>Lithium</term><term>Ltmp</term><term>Methyl</term><term>Methyl carbon</term><term>Mmol</term><term>Proximity effect</term><term>Pyridine</term><term>Pyridine derivatives</term><term>Reaction mixture</term><term>Regioselective</term><term>Regioselective lithiation</term><term>Regioselective ring lithiation</term><term>Relative stability</term><term>Ring lithiation</term><term>Room temperature</term><term>Sch3 sech3</term><term>Sech3</term><term>Selenium</term><term>Singh</term><term>Verlag</term><term>Verlag gmbh</term><term>Weinheim</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract">The regioselective ring lithiation of BF3‐complexed 3‐picoline (1a), 3,4‐lutidine (1b), and 3,5‐lutidine (1c) was studied. The dilithiation of 1a, 1b, and 1c was also investigated to experimentally explore the relative preference of the sites on the substituted pyridine ring for lithiation. The role of the complex‐induced proximity effect (CIPE) for inducing lithiation in these moieties was investigated using both experimental and computational studies.</div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
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