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Rhodium‐Catalyzed Transnitrilation of Aryl Boronic Acids with Dimethylmalononitrile
Author(s) -
Malapit Christian A.,
Reeves Jonathan T.,
Busacca Carl A.,
Howell Amy R.,
Senanayake Chris H.
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.201508122
Subject(s) - rhodium , aryl , catalysis , chemistry , organic chemistry , boronic acid , combinatorial chemistry , alkyl
An efficient transnitrilation of aryl boronic acids with dimethylmalononitrile (DMMN) is described. This rhodium‐catalyzed electrophilic cyanation presents a novel approach to prepare aryl nitriles by using a carbon‐bound cyanating reagent which undergoes cross‐coupling with the aryl boronic acid. The reaction expands the degree of functional‐group compatibility exhibited by the transnitrilation of aryl Grignard and aryllithium reagents. A variety of aryl boronic acid derivatives and dialkylmalononitriles were amenable to the transnitrilation.