Gold-Catalyzed Oxidation of Thioalkynes To Form Phenylthio Ketene Derivatives via a Noncarbene Route

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 den...

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Bibliographic Details
Published in:Organic letters 2019-07, Vol.21 (14), p.5475-5479
Main Authors: Sharma, Pankaj, Singh, Rahulkumar Rajmani, Giri, Sovan Sundar, Chen, Liang-Yu, Cheng, Mu-Jeng, Liu, Rai-Shung
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01768