Journal
ORGANIC LETTERS
Volume 22, Issue 4, Pages 1375-1379Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04664
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Funding
- MEXT [17H06091]
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The synthesis of indanone derivatives by the Rh(III)-catalyzed reaction of alpha-carbonyl sulfoxonium ylides with activated alkenes is reported. The reaction shows a high tolerance for functional groups and furnishes a variety of substituted indanone derivatives via a formal [4 + 1] cycloaddition. Highly stable sulfoxonium ylides were used as substrates in this C-H functionalization, and their bifunctional character could be effectively exploited using Rh(III) catalysis via sequential double C-C bond formation. Based on mechanistic studies including deuterium-labeling experiments, the reaction is proposed to proceed as follows: Rh(III)-catalyzed C-H oxidative alkenylation via beta-hydride elimination, readdition of H-Rh species, a 1,2-carbon shift with the elimination of DMSO, and protonation.
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