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Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes
Author(s) -
Zhong Mingbing,
Gagné Yohann,
Hope Taylor O.,
Pannecoucke Xavier,
Frenette Mathieu,
Jubault Philippe,
Poisson Thomas
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202101874
Subject(s) - hydroboration , chemistry , photocatalysis , copper , boron , radical , flow chemistry , continuous flow , photochemistry , functional group , organic chemistry , catalysis , physics , polymer , mechanics
The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly‐designed copper photocatalysts with B 2 Pin 2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions were developed under continuous flow conditions to demonstrate their synthetic utility. The reaction mechanism was studied and suggested an oxidation reaction between an in situ formed borate and the Cu‐photocatalyst in its excited state for the boryl radical formation.