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Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β‐Ketonitrile Derivatives
Author(s) -
Kiyokawa Kensuke,
Nagata Takaya,
Minakata Satoshi
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605445
Subject(s) - cyanation , electrophile , boron , enantioselective synthesis , cyanide , reagent , chemistry , substrate (aquarium) , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology
The highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N ‐cyano‐ N ‐phenyl‐ p ‐toluenesulfonamide (NCTS) and p ‐toluenesulfonyl cyanide (TsCN), is reported. Various β‐ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of β‐ketonitriles containing a quaternary α‐carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described.
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