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C−H Cyanation of 6‐Ring N‐Containing Heteroaromatics
Author(s) -
Elbert Bryony L.,
Farley Alistair J. M.,
Gorman Timothy W.,
Johnson Tarn C.,
Genicot Christophe,
Lallemand Bénédicte,
Pasau Patrick,
Flasz Jakub,
Castro José L.,
MacCoss Malcolm,
Paton Robert S.,
Schofield Christopher J.,
Smith Martin D.,
Willis Michael C.,
Dixon Darren J.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703931
Subject(s) - cyanation , ring (chemistry) , chemistry , stereochemistry , organic chemistry , catalysis
Abstract Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far‐reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C−H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one‐pot protocol is simple to perform, is applicable to a broad range of decorated 6‐ring N‐containing heterocycles, and has been shown to be suitable for late‐stage functionalization of complex drug‐like architectures.