Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds

Abstract

Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation of N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal- and catalyst-free conditions. This method exhibits a broad substrate scope, high functional group tolerance, and high regioselectivity. Furthermore, this strategy provides straightforward access to a range of derivatives through the subsequent elaboration of the xanthate group.

Keywords

• C-H functionalization
• 1,5-Hydrogen atom transfer
• Photocatalytic
• Site-specific
• Xanthylation