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Published on: June 21, 2017
Photoredox-catalyzed cyclopropanation of allenes towards vinyl-cyclopropanes
Hui Xie1, Yan Zhang1, Bernhard Breit1
1Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg Albertstraße 21 79104 Freiburg im Breisgau Germany bernhard.breit@chemie.uni-freiburg.de.
Abstract:
While the vinyl cyclopropane (VCP) scaffold exhibits unique reactivity in chemical transformations, its synthesis presents certain challenges. Herein, we report the visible-light photoredox-catalyzed radical-polar crossover cyclization (RPCC) of terminal and internal allenes with carboxylic acids, realizing the construction of functionalized vinyl cyclopropanes (VCPs) with highly chemo-, and regioselectivities under mild conditions. Moreover, this photoredox protocol exhibits good functional group tolerance, a broad substrate scope, facile scalability and easy rearrangement to give various cyclopentene units.
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