Issue 40, 2022

Phosphine-catalyzed hydroboration of propiolonitriles: access to (E)-1,2-vinylcyanotrifluoroborate derivatives

Abstract

We report an organocatalytic trans hydroboration of 3-substituted-propiolonitriles. In the presence of catalytic amounts of tributylphosphine and pinacolborane, regioselective hydroboration of the internal triple bond proceeded in a stereoselective fashion under mild conditions to afford the corresponding (E)-1,2-vinylcyanoborane derivatives. The mechanism is proposed to occur through a 1,2-phosphine addition instead of a canonical 1,4-conjugate addition pathway.

Graphical abstract: Phosphine-catalyzed hydroboration of propiolonitriles: access to (E)-1,2-vinylcyanotrifluoroborate derivatives

Supplementary files

Article information

Article type
Communication
Submitted
01 fev 2022
Accepted
22 apr 2022
First published
22 apr 2022

Chem. Commun., 2022,58, 5984-5987

Author version available

Phosphine-catalyzed hydroboration of propiolonitriles: access to (E)-1,2-vinylcyanotrifluoroborate derivatives

J. Bowen, C. Slebodnick and W. L. Santos, Chem. Commun., 2022, 58, 5984 DOI: 10.1039/D2CC00603K

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