BI-OAc-Accelerated C3-H Alkylation of Quinoxalin-2(1 H)-ones under Visible-Light Irradiation

Org Lett. 2020 Aug 7;22(15):5984-5989. doi: 10.1021/acs.orglett.0c02080. Epub 2020 Jul 24.


An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules.

Publication types

  • Research Support, Non-U.S. Gov't