Light‐Induced Divergent Cyanation of Alkynes Enabled by Phosphorus Radicals

A photochemically induced selective and divergent cyanation reaction of alkynes, enabled by phosphorus radicals, is described. With the use of simple triarylphosphine as a co‐catalyst, three cyanation reactions, including di‐hydrocyanation, anti‐Markovnikov hydrocyanation, and domino hydrocyanation/...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-12, Vol.61 (50), p.e202210838-n/a
Main Authors: Zhang, Yanyan, Han, Yunhong, Zhu, Shengqing, Qing, Feng‐Ling, Xue, Xiao‐Song, Chu, Lingling
Format: Article
Language:English
Subjects:
Alkynes
Biological activity
Catalysts
Computer applications
Cyanation
Cyanides
Divergence
Nitriles
Phosphines
Phosphorus
Photoredox Catalysis
Radicals
Selectivity
Synthetic Methods
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Summary:A photochemically induced selective and divergent cyanation reaction of alkynes, enabled by phosphorus radicals, is described. With the use of simple triarylphosphine as a co‐catalyst, three cyanation reactions, including di‐hydrocyanation, anti‐Markovnikov hydrocyanation, and domino hydrocyanation/reduction, can be divergently achieved, furnishing a wide array of alkyl dinitriles, alkenyl nitriles, and alkyl nitriles under mild conditions. Terminal and internal alkynes are applicable with high efficiency and excellent selectivity. Synthetic applications for biologically active agents and preliminary experimental and computational mechanistic studies are reported. A photochemically induced selective and divergent cyanation reaction of alkynes, enabled by phosphorus radicals, is described. With the use of simple triarylphosphine as a co‐catalyst, three cyanation reactions, including di‐hydrocyanation, anti‐Markovnikov hydrocyanation, and domino hydrocyanation/reduction, can be divergently achieved, furnishing a wide array of alkyl dinitriles, alkenyl nitriles, and alkyl nitriles under mild conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202210838