Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions.
Morgane SayesGuillaume BenoitAndré B CharettePublished in: Angewandte Chemie (International ed. in English) (2018)
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.