Journal
ORGANIC LETTERS
Volume 18, Issue 12, Pages 3034-3037Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01470
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Funding
- FAPESP (Research Supporting Foundation of the State of Sao Paulo) [2013/25504-1, 2013/18009-4]
- CNPq [301079/2012-9, 2011/160522-0]
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Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing beta-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room temperature. Additional experimental as well as kinetic isotopic effect studies give some insight into the mechanism of this reaction.
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