Affiliation:
1. Department of Applied Chemistry Graduate School of Engineering Osaka University Yamadaoka 2-1 Suita, Osaka 565-0871 Japan
Abstract
AbstractOxycyanation of alkenes would allow the direct construction of useful β‐hydroxy nitrile scaffolds. However, only limited examples of such reactions have been reported, and some problems including limited substrate scope and the lack of diastereocontrol in the case of the oxycyanation of internal alkenes have arisen. We herein report on the intermolecular oxycyanation of alkenes using p‐toluenesulfonyl cyanide (TsCN) in the presence of tris(pentafluorophenyl)borane (B(C6F5)3) as a catalyst, affording products that contain a sulfinyloxy group and a cyano group at the vicinal position. The reaction features a stereospecific syn‐addition. The reaction also shows a broad substrate scope with good functional group tolerance. Mechanistic investigations by experimental studies and density functional theory (DFT) calculations revealed that the reaction proceeds via an unprecedented stereospecific mechanism through the electrophilic cyanation of alkenes, in which B(C6F5)3 efficiently activates TsCN through the coordination of the cyano group to the boron center.
Funder
Japan Society for the Promotion of Science
Asahi Glass Foundation
Uehara Memorial Foundation
Subject
General Chemistry,Catalysis
Cited by
2 articles.
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