Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
Identifieur interne : 000A72 ( Main/Repository ); précédent : 000A71; suivant : 000A73Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
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Abstract
The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32 h to 10-70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation</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 Química, Universidad Nacional del Sur, Avenida Alem 1253</s1><s2>Bahia Blanca B8000CPB</s2><s3>ARG</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Argentine</country><wicri:noRegion>Bahia Blanca B8000CPB</wicri:noRegion></affiliation></author><author><name sortKey="Badajoz, Mercedes A" uniqKey="Badajoz M">Mercedes A. Badajoz</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253</s1><s2>Bahia Blanca B8000CPB</s2><s3>ARG</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Argentine</country><wicri:noRegion>Bahia Blanca B8000CPB</wicri:noRegion></affiliation></author><author><name sortKey="Domini, Claudia" uniqKey="Domini C">Claudia Domini</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253</s1><s2>Bahia Blanca B8000CPB</s2><s3>ARG</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Argentine</country><wicri:noRegion>Bahia 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 Química, Universidad Nacional del Sur, Avenida Alem 1253</s1><s2>Bahia Blanca B8000CPB</s2><s3>ARG</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Argentine</country><wicri:noRegion>Bahia Blanca B8000CPB</wicri:noRegion></affiliation></author><author><name sortKey="Lockhart, Mar A T" uniqKey="Lockhart M">Mar A T. Lockhart</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253</s1><s2>Bahia Blanca B8000CPB</s2><s3>ARG</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Argentine</country><wicri:noRegion>Bahia Blanca B8000CPB</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="inist">13-0125663</idno><date when="2013">2013</date><idno type="stanalyst">PASCAL 13-0125663 INIST</idno><idno type="RBID">Pascal:13-0125663</idno><idno type="wicri:Area/Main/Corpus">001079</idno><idno type="wicri:Area/Main/Repository">000A72</idno></publicationStmt><seriesStmt><idno type="ISSN">1350-4177</idno><title level="j" type="abbreviated">Ultrason. sonochem.</title><title level="j" type="main">Ultrasonics sonochemistry</title></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Indium</term><term>Ketone</term><term>Regioselectivity</term><term>Sonochemistry</term><term>Synthesis</term><term>Ultrasound</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Indium</term><term>Régiosélectivité</term><term>Synthèse</term><term>Cétone</term><term>Ultrason</term><term>Sonochimie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32 h to 10-70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>1350-4177</s0></fA01><fA03 i2="1"><s0>Ultrason. sonochem.</s0></fA03><fA05><s2>20</s2></fA05><fA06><s2>3</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation</s1></fA08><fA11 i1="01" i2="1"><s1>LO FIEGO (Marcos J.)</s1></fA11><fA11 i1="02" i2="1"><s1>BADAJOZ (Mercedes A.)</s1></fA11><fA11 i1="03" i2="1"><s1>DOMINI (Claudia)</s1></fA11><fA11 i1="04" i2="1"><s1>CHOPA (Alicia B.)</s1></fA11><fA11 i1="05" i2="1"><s1>LOCKHART (María T.)</s1></fA11><fA14 i1="01"><s1>Instituto de Quimica del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253</s1><s2>Bahia Blanca B8000CPB</s2><s3>ARG</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ></fA14><fA20><s1>826-832</s1></fA20><fA21><s1>2013</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>11021A</s2><s5>354000502400360070</s5></fA43><fA44><s0>0000</s0><s1>© 2013 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>23 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>13-0125663</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Ultrasonics sonochemistry</s0></fA64><fA66 i1="01"><s0>GBR</s0></fA66><fC01 i1="01" l="ENG"><s0>The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32 h to 10-70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. 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