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

Kieran Benn, Kieran Nicholson, Thomas Langer, Stephen P. Thomas

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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.
Original languageEnglish
JournalChemical Communications
Early online date24 Aug 2021
DOIs
Publication statusE-pub ahead of print - 24 Aug 2021

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