Gold-Catalyzed Oxidation of Thioalkynes To Form Phenylthio Ketene Derivatives via a Noncarbene Route.
Org Lett, 2019/7/19;21(14):5475-5479.
Sharma P[1], Singh RR[1], Giri SS[1], Chen LY[2], Cheng MJ[2], Liu RS[1]
Affiliations
PMID: 31274331DOI: 10.1021/acs.orglett.9b01768
Impact factor: 6.072
Abstract
Gold-catalyzed oxidations of thioalkynes with 8-methylquinoline oxides afford 2-phenylthioketenes that can be trapped efficiently with alcohols. The synthetic utility is manifested by terminal and internal thioalkynes over a wide scope, bearing esters, ketones, alkyl, and oxime substituents. Our density functional theory calculations suggest that gold-catalyzed oxidations of terminal and internal thioalkynes with 8-methylquinoline oxides generate gold-bound ketene intermediates without the intermediacy of α-oxo gold carbene.
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