Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 14, Pages 9677-9685Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02910
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This study presents the development of the Rh-catalyzed[2,3]-sigmatropic rearrangement of alkynyl carbenes with allyl sulfides. The protocol shows good tolerance towards various functional groups and enables the synthesis of valuable sulfide-substituted 1,5-enyne products. It is the first example of [2,3]-sigmatropic rearrangement of alkynyl carbenes. DFT analysis confirms the involvement of rhodium carbene generation, sulfoniumylides formation, and [2,3]-sigmatropic rearrangement pathway.
This study describes the development of Rh-catalyzed[2,3]-sigmatropicrearrangement of alkynyl carbenes with allyl sulfides. The protocolexhibits equitable functional group tolerance and allows the formationof a variety of synthetically valuable sulfide-substituted 1,5-enyneproducts. To the best of our knowledge, this is the first exampleof [2,3]-sigmatropic rearrangement of alkynyl carbenes. DFT analysissupports the involvement of rhodium carbene generation, sulfoniumylides formation, and [2,3]-sigmatropic rearrangement pathway.
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