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 jul 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

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