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Borocyclopropanation of Styrenes Mediated by UV‐light Under Continuous Flow Conditions
Author(s) -
Sayes Morgane,
Benoit Guillaume,
Charette André B.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201807347
Subject(s) - styrene , photosensitizer , photochemistry , quenching (fluorescence) , chemistry , continuous flow , xanthone , residence time (fluid dynamics) , combinatorial chemistry , organic chemistry , fluorescence , copolymer , biochemical engineering , polymer , physics , quantum mechanics , engineering , geotechnical engineering
Herein, we report a user‐friendly and metal‐free UV‐A light mediated borocyclopropanation of styrenes using continuous flow technology. A broad range of styrene derivatives can be cyclopropanated in good yields within 1 h residence time to produce highly valuable cyclopropylboronate esters with modest to good diastereoselectivities. The reaction is also applicable to α‐substituted styrenes. Mechanistic studies support a photoredox process during which xanthone, a well‐known organic photosensitizer, can easily reach a photoexcited state that is available for both an oxidative and a reductive quenching.