Issue 74, 2021

A boron–nitrogen transborylation enabled, borane-catalysed reductive cyanation of enones

Abstract

Cyanation offers a simple method for the introduction of a nitrile group into organic molecules and an orthogonal route for the installation of a wide array of functional groups using simple transformations. Cyanation methods are dominated by transition metal catalysis and the use of hydrogen cyanide gas. Here, the electrophilic cyanation of enones was achieved using a main-group catalyst and a non-toxic, electrophilic cyanide source. This protocol was applied across a broad substrate scope including those containing reducible functional groups. Mechanistic studies indicated an amino-borane intermediate which underwent B–N transborylation (B–N/B–H exchange) to achieve catalytic turnover.

Graphical abstract: A boron–nitrogen transborylation enabled, borane-catalysed reductive cyanation of enones

Supplementary files

Article information

Article type
Communication
Submitted
07 Jūl. 2021
Accepted
17 Aug. 2021
First published
24 Aug. 2021
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2021,57, 9406-9409

A boron–nitrogen transborylation enabled, borane-catalysed reductive cyanation of enones

K. Benn, K. Nicholson, T. Langer and S. P. Thomas, Chem. Commun., 2021, 57, 9406 DOI: 10.1039/D1CC03649A

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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