Issue 40, 2017

Copper(i)-catalyzed 5-exo-trig radical cyclization/borylation of alkyl halides: access to functionalized pyrrolidine derivatives

Abstract

This work reports the copper(I)-catalyzed 5-exo-trig radical cyclization/borylation of alkyl halides bearing an alkene moiety, during which a C–C bond and a C–B bond were formed in one step. Various functionalized pyrrolidine derivatives bearing a quaternary carbon center were obtained, and they showed good functional group tolerance and high chemoselectivity. This transformation was highly efficient and could be finished in 20 minutes. A radical mechanism has been proposed.

Graphical abstract: Copper(i)-catalyzed 5-exo-trig radical cyclization/borylation of alkyl halides: access to functionalized pyrrolidine derivatives

Supplementary files

Article information

Article type
Communication
Submitted
24 Jul 2017
Accepted
25 Sep 2017
First published
25 Sep 2017

Org. Biomol. Chem., 2017,15, 8508-8512

Copper(I)-catalyzed 5-exo-trig radical cyclization/borylation of alkyl halides: access to functionalized pyrrolidine derivatives

J. Cui, H. Wang, J. Song, X. Chi, L. Meng, Q. Liu, D. Zhang, Y. Dong and H. Liu, Org. Biomol. Chem., 2017, 15, 8508 DOI: 10.1039/C7OB01831B

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