PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones
(Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yields. The salient features of this reaction are that it emp...
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th-mahidol.289172018-09-24T15:52:55Z PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones Praewpan Katrun Supanimit Chiampanichayakul Kanokwan Korworapan Manat Pohmakotr Vichai Reutrakul Thaworn Jaipetch Chutima Kuhakarn Mahidol University Chemistry (Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yields. The salient features of this reaction are that it employs a commercially available and environmentally benign hypervalent iodine(III) reagent, a one-step reaction, a short reaction time, and mild reaction conditions. (Diacetoxyiodo)benzene/KI was able to promote the reaction of sodium aryl sulfinates with alkenes to afford vinyl sulfones in good yields. Alkynes underwent a similar reaction to give β-iodovinyl sulfones. The present method can be considered to be a convenient and attractive alternative to the existing methods for the synthesis of these intermediates, which are important in organic chemistry. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 2018-09-24T08:52:55Z 2018-09-24T08:52:55Z 2010-10-01 Article European Journal of Organic Chemistry. No.29 (2010), 5633-5641 10.1002/ejoc.201000641 10990690 1434193X 2-s2.0-78249261544 https://repository.li.mahidol.ac.th/handle/123456789/28917 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=78249261544&origin=inward |
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Chemistry Praewpan Katrun Supanimit Chiampanichayakul Kanokwan Korworapan Manat Pohmakotr Vichai Reutrakul Thaworn Jaipetch Chutima Kuhakarn PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones |
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(Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yields. The salient features of this reaction are that it employs a commercially available and environmentally benign hypervalent iodine(III) reagent, a one-step reaction, a short reaction time, and mild reaction conditions. (Diacetoxyiodo)benzene/KI was able to promote the reaction of sodium aryl sulfinates with alkenes to afford vinyl sulfones in good yields. Alkynes underwent a similar reaction to give β-iodovinyl sulfones. The present method can be considered to be a convenient and attractive alternative to the existing methods for the synthesis of these intermediates, which are important in organic chemistry. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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Mahidol University |
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Mahidol University Praewpan Katrun Supanimit Chiampanichayakul Kanokwan Korworapan Manat Pohmakotr Vichai Reutrakul Thaworn Jaipetch Chutima Kuhakarn |
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Praewpan Katrun Supanimit Chiampanichayakul Kanokwan Korworapan Manat Pohmakotr Vichai Reutrakul Thaworn Jaipetch Chutima Kuhakarn |
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Praewpan Katrun |
title |
PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones |
title_short |
PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones |
title_full |
PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones |
title_fullStr |
PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones |
title_full_unstemmed |
PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones |
title_sort |
phi(oac)2/ki-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: synthesis of vinyl sulfones and β-iodovinyl sulfones |
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2018 |
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https://repository.li.mahidol.ac.th/handle/123456789/28917 |
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1763495286287630336 |