Photoinduced EDA Complexes Enabled Radical Tandem Cyclization/Arylation of Unactivated Alkene with 2-Amino-1,4-naphthoquinones

Org Lett. 2021 Mar 5;23(5):1862-1867. doi: 10.1021/acs.orglett.1c00268. Epub 2021 Feb 19.

Abstract

A visible-light-induced radical tandem cyclization/arylation between 2-amino-1, 4-naphthoquinone and N-allyl-2-bromo-2,2-difluoroacetamides has been developed without an external photocatalyst. The transformation could be carried out at room temperature and gave a variety of C-3-functionalized 2-amino-1,4-naphthoquinone derivatives in moderate to excellent yields. Moreover, mechanistic studies revealed that the reaction is driven by the formation of an electron donor-acceptor (EDA) complex.