Regioselective Radical Borylation of α,β-Unsaturated Esters and Related Compounds by Visible Light Irradiation with an Organic Photocatalyst

Radical hydroboration reactions have only recently been reported and are still rare. Here we describe a photoredox radical hydroboration of α,β-unsaturated esters, amides, ketones, and nitriles with NHC-boranes that uses only an organocatalyst and visible light. The conditions are mild, the substrat...

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Bibliographic Details
Published in:Organic letters 2021-06, Vol.23 (11), p.4353-4357
Main Authors: Li, Guosong, Huang, Guanwang, Sun, Ruixia, Curran, Dennis P, Dai, Wen
Format: Article
Language:English
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Summary:Radical hydroboration reactions have only recently been reported and are still rare. Here we describe a photoredox radical hydroboration of α,β-unsaturated esters, amides, ketones, and nitriles with NHC-boranes that uses only an organocatalyst and visible light. The conditions are mild, the substrate scope is broad, and the α/β regioselectivity is high. The reaction requires only the organocatalyst; there is no costly metal, and there are no other additives (base, cocatalyst, initiator).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01270