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 فرؤری 2022
Accepted
22 اپریل 2022
First published
22 اپریل 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements