Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(C₆F₅)₃ Enabling the Electrophilic Cyanation of Silyl Enol Ethers

Takaya Nagata, Hiroki Matsubara, Kensuke Kiyokawa* and Satoshi Minakata*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Email: kiyokawachem.eng.osaka-u.ac.jp, minakatachem.eng.osaka-u.ac.jp

T. Nagata, H. Matsubara, K. Kiyokawa, S. Minakata, Org. Lett., 2017, 19, 4672-4675.

DOI: 10.1021/acs.orglett.7b02313

Abstract

A Lewis acidic activation of a hypervalent iodine reagent containing a transferable cyano group achieves a catalytic electrophilic cyanation of silyl enol ethers. Mechanistic studies indicate that the hypervalent iodine reagent is activated through coordination of its cyano group to B(C₆F₅)₃.

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proposed mechanism

Key Words

cyanation

ID: J54-Y2017

Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(C6F5)3 Enabling the Electrophilic Cyanation of Silyl Enol Ethers

Takaya Nagata, Hiroki Matsubara, Kensuke Kiyokawa* and Satoshi Minakata*

Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(C₆F₅)₃ Enabling the Electrophilic Cyanation of Silyl Enol Ethers