Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic at...

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Main Authors: Haruo Aikawa, Tetsuro Kaneko, Naoki Asao, Yoshinori Yamamoto
Format: Article
Language:English
Published: Beilstein-Institut 2011-05-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.7.76
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author Haruo Aikawa
Tetsuro Kaneko
Naoki Asao
Yoshinori Yamamoto
author_facet Haruo Aikawa
Tetsuro Kaneko
Naoki Asao
Yoshinori Yamamoto
author_sort Haruo Aikawa
collection DOAJ
description Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.
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spelling doaj.art-79d0e7fc19b04d109173d112b04cd82a2022-12-21T23:27:53ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-05-017164865210.3762/bjoc.7.761860-5397-7-76Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid estersHaruo Aikawa0Tetsuro Kaneko1Naoki Asao2Yoshinori Yamamoto3Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanUnprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.https://doi.org/10.3762/bjoc.7.76alkylationgold catalysisleaving groupsilyl enol ethersubstitution reaction
spellingShingle Haruo Aikawa
Tetsuro Kaneko
Naoki Asao
Yoshinori Yamamoto
Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
Beilstein Journal of Organic Chemistry
alkylation
gold catalysis
leaving group
silyl enol ether
substitution reaction
title Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_full Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_fullStr Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_full_unstemmed Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_short Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_sort gold catalyzed alkylation of silyl enol ethers with ortho alkynylbenzoic acid esters
topic alkylation
gold catalysis
leaving group
silyl enol ether
substitution reaction
url https://doi.org/10.3762/bjoc.7.76
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AT tetsurokaneko goldcatalyzedalkylationofsilylenoletherswithorthoalkynylbenzoicacidesters
AT naokiasao goldcatalyzedalkylationofsilylenoletherswithorthoalkynylbenzoicacidesters
AT yoshinoriyamamoto goldcatalyzedalkylationofsilylenoletherswithorthoalkynylbenzoicacidesters