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C-H cyanation of 6-ring N-containing heteroaromatics

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.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1002/chem.201703931

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author


Publisher:
Wiley
Journal:
Chemistry - A European Journal More from this journal
Volume:
23
Issue:
59
Pages:
14733-14737
Publication date:
2017-08-23
Acceptance date:
2017-08-22
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
Pmid:
28833674


Language:
English
Keywords:
Pubs id:
pubs:724085
UUID:
uuid:e867361a-2ddf-46bf-a8c6-e13bb629866e
Local pid:
pubs:724085
Deposit date:
2017-10-06

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