Visible-Light-Mediated N-Desulfonylation of N-Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst

J Org Chem. 2020 Jul 2;85(13):8732-8739. doi: 10.1021/acs.joc.0c00983. Epub 2020 Jun 16.

Abstract

A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF4, has been developed for the photodeprotection of benzenesulfonyl-protected N-heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the N-heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't