IndiumV3, Main, Repository, bibRecord, 002586

Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes

Identifieur interne : 002586 ( Main/Repository ); précédent : 002585; suivant : 002587

Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes

Auteurs : RBID : Pascal:11-0256816

Descripteurs français

Pascal (Inist)
- Sélectivité, Synthèse chimique, Encombrement stérique, Molécule asymétrique, Cétone, Chlore composé organique, Dérivé de la benzophénone, Isolement, Température ambiante, Aluminium III Chlorure, Méthane(dichloro), Réaction sans solvant, Indium, Mécanisme radicalaire, Stannane organique, Composé benzénique, Hydrocarbure chloré, Réaction sans catalyseur, Benzène(1,2-dichloro).

English descriptors

KwdEn :
- Aluminium III Chlorides, Asymmetric molecule, Benzenic compound, Benzophenone derivatives, Chemical synthesis, Chlorocarbon, Dichloromethane, Indium, Isolation, Ketone, Organic chlorine compounds, Organic stannane, Radical mechanism, Room temperature, Selectivity, Solvent free reaction, Steric hindrance.

Abstract

Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl₃ (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.

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Pascal:11-0256816

Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes</title>
<author><name sortKey="Lo Fiego, Marcos J" uniqKey="Lo Fiego M">Marcos J. Lo Fiego</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET - UNS), Departamento de Quimica, Universidad Nacional del Sur, Avenida Alem 1253</s1>
<s2>Bahía Blanca, B8000CPB</s2>
<s3>ARG</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Argentine</country>
<wicri:noRegion>Bahía Blanca, B8000CPB</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Silbestri, Gustavo F" uniqKey="Silbestri G">Gustavo F. Silbestri</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET - UNS), Departamento de Quimica, Universidad Nacional del Sur, Avenida Alem 1253</s1>
<s2>Bahía Blanca, B8000CPB</s2>
<s3>ARG</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Argentine</country>
<wicri:noRegion>Bahía Blanca, B8000CPB</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Chopa, Alicia B" uniqKey="Chopa A">Alicia B. Chopa</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET - UNS), Departamento de Quimica, Universidad Nacional del Sur, Avenida Alem 1253</s1>
<s2>Bahía Blanca, B8000CPB</s2>
<s3>ARG</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Argentine</country>
<wicri:noRegion>Bahía Blanca, B8000CPB</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Lockhart, Maria T" uniqKey="Lockhart M">Maria T. Lockhart</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET - UNS), Departamento de Quimica, Universidad Nacional del Sur, Avenida Alem 1253</s1>
<s2>Bahía Blanca, B8000CPB</s2>
<s3>ARG</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Argentine</country>
<wicri:noRegion>Bahía Blanca, B8000CPB</wicri:noRegion>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="inist">11-0256816</idno>
<date when="2011">2011</date>
<idno type="stanalyst">PASCAL 11-0256816 INIST</idno>
<idno type="RBID">Pascal:11-0256816</idno>
<idno type="wicri:Area/Main/Corpus">003074</idno>
<idno type="wicri:Area/Main/Repository">002586</idno>
</publicationStmt>
<seriesStmt><idno type="ISSN">0022-3263</idno>
<title level="j" type="abbreviated">J. org. chem.</title>
<title level="j" type="main">Journal of organic chemistry</title>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aluminium III Chlorides</term>
<term>Asymmetric molecule</term>
<term>Benzenic compound</term>
<term>Benzophenone derivatives</term>
<term>Chemical synthesis</term>
<term>Chlorocarbon</term>
<term>Dichloromethane</term>
<term>Indium</term>
<term>Isolation</term>
<term>Ketone</term>
<term>Organic chlorine compounds</term>
<term>Organic stannane</term>
<term>Radical mechanism</term>
<term>Room temperature</term>
<term>Selectivity</term>
<term>Solvent free reaction</term>
<term>Steric hindrance</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Sélectivité</term>
<term>Synthèse chimique</term>
<term>Encombrement stérique</term>
<term>Molécule asymétrique</term>
<term>Cétone</term>
<term>Chlore composé organique</term>
<term>Dérivé de la benzophénone</term>
<term>Isolement</term>
<term>Température ambiante</term>
<term>Aluminium III Chlorure</term>
<term>Méthane(dichloro)</term>
<term>Réaction sans solvant</term>
<term>Indium</term>
<term>Mécanisme radicalaire</term>
<term>Stannane organique</term>
<term>Composé benzénique</term>
<term>Hydrocarbure chloré</term>
<term>Réaction sans catalyseur</term>
<term>Benzène(1,2-dichloro)</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl<sub>3</sub>
 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.</div>
</front>
</TEI>
<inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0022-3263</s0>
</fA01>
<fA02 i1="01"><s0>JOCEAH</s0>
</fA02>
<fA03 i2="1"><s0>J. org. chem.</s0>
</fA03>
<fA05><s2>76</s2>
</fA05>
<fA06><s2>6</s2>
</fA06>
<fA08 i1="01" i2="1" l="ENG"><s1>Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes</s1>
</fA08>
<fA11 i1="01" i2="1"><s1>LO FIEGO (Marcos J.)</s1>
</fA11>
<fA11 i1="02" i2="1"><s1>SILBESTRI (Gustavo F.)</s1>
</fA11>
<fA11 i1="03" i2="1"><s1>CHOPA (Alicia B.)</s1>
</fA11>
<fA11 i1="04" i2="1"><s1>LOCKHART (Maria T.)</s1>
</fA11>
<fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET - UNS), Departamento de Quimica, Universidad Nacional del Sur, Avenida Alem 1253</s1>
<s2>Bahía Blanca, B8000CPB</s2>
<s3>ARG</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
</fA14>
<fA20><s1>1707-1714</s1>
</fA20>
<fA21><s1>2011</s1>
</fA21>
<fA23 i1="01"><s0>ENG</s0>
</fA23>
<fA43 i1="01"><s1>INIST</s1>
<s2>602</s2>
<s5>354000194432420220</s5>
</fA43>
<fA44><s0>0000</s0>
<s1>© 2011 INIST-CNRS. All rights reserved.</s1>
</fA44>
<fA45><s0>28 ref.</s0>
</fA45>
<fA47 i1="01" i2="1"><s0>11-0256816</s0>
</fA47>
<fA60><s1>P</s1>
</fA60>
<fA61><s0>A</s0>
</fA61>
<fA64 i1="01" i2="1"><s0>Journal of organic chemistry</s0>
</fA64>
<fA66 i1="01"><s0>USA</s0>
</fA66>
<fC01 i1="01" l="ENG"><s0>Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl<sub>3</sub>
 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>001C03C03</s0>
</fC02>
<fC02 i1="02" i2="X"><s0>001C03B02</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE"><s0>Sélectivité</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG"><s0>Selectivity</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Selectividad</s0>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE"><s0>Synthèse chimique</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG"><s0>Chemical synthesis</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Síntesis química</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE"><s0>Encombrement stérique</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Steric hindrance</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Embarazo estérico</s0>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Molécule asymétrique</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Asymmetric molecule</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Molécula asimétrica</s0>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Cétone</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Ketone</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Cetona</s0>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="3" l="FRE"><s0>Chlore composé organique</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="3" l="ENG"><s0>Organic chlorine compounds</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Dérivé de la benzophénone</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Benzophenone derivatives</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Benzofenona derivado</s0>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Isolement</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Isolation</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Aislamiento</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Température ambiante</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Room temperature</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Temperatura ambiente</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Aluminium III Chlorure</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Aluminium III Chlorides</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Aluminio III Cloruro</s0>
<s2>NC</s2>
<s2>NA</s2>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Méthane(dichloro)</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Dichloromethane</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Metano(dicloro)</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>11</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Réaction sans solvant</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Solvent free reaction</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Reacción sin solvente</s0>
<s5>12</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Indium</s0>
<s2>NC</s2>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Indium</s0>
<s2>NC</s2>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Indio</s0>
<s2>NC</s2>
<s5>13</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Mécanisme radicalaire</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Radical mechanism</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>Mecanismo radicalar</s0>
<s5>14</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Stannane organique</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>Organic stannane</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA"><s0>Estannano orgánico</s0>
<s5>15</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Composé benzénique</s0>
<s5>41</s5>
</fC03>
<fC03 i1="16" i2="X" l="ENG"><s0>Benzenic compound</s0>
<s5>41</s5>
</fC03>
<fC03 i1="16" i2="X" l="SPA"><s0>Compuesto bencénico</s0>
<s5>41</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE"><s0>Hydrocarbure chloré</s0>
<s5>42</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG"><s0>Chlorocarbon</s0>
<s5>42</s5>
</fC03>
<fC03 i1="17" i2="X" l="SPA"><s0>Hidrocarburo clorado</s0>
<s5>42</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE"><s0>Réaction sans catalyseur</s0>
<s4>INC</s4>
<s5>62</s5>
</fC03>
<fC03 i1="19" i2="X" l="FRE"><s0>Benzène(1,2-dichloro)</s0>
<s4>INC</s4>
<s5>64</s5>
</fC03>
<fN21><s1>171</s1>
</fN21>
</pA>
</standard>
</inist>
</record>

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Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes

Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

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