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Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(CF) Enabling the Electrophilic Cyanation of Silyl Enol Ethers. | LitMetric

Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(CF) Enabling the Electrophilic Cyanation of Silyl Enol Ethers.

Org Lett

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.

Published: September 2017

The Lewis acidic activation of a hypervalent iodine reagent containing a transferable cyano group, 1-cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole (CDBX), with B(CF), to achieve the catalytic electrophilic cyanation of silyl enol ethers is presented. Mechanistic studies indicate that CDBX is activated through coordination of its cyano group to B(CF), thus enabling the electrophilic cyanation reaction to occur.

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Source
http://dx.doi.org/10.1021/acs.orglett.7b02313DOI Listing

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