Visible-Light-Induced C(sp3)-H Activation for Minisci Alkylation of Pyrimidines Using CHCl3 as Radical Source and Oxidant

Jiatian Zhuo; Jinshan Liu; Min Zhou; Lin Ma; Min Zhang

doi:10.1021/acs.joc.4c02855

Visible-Light-Induced C(sp³)-H Activation for Minisci Alkylation of Pyrimidines Using CHCl₃ as Radical Source and Oxidant

J Org Chem. 2025 Jan 14. doi: 10.1021/acs.joc.4c02855. Online ahead of print.

Authors

Jiatian Zhuo¹, Jinshan Liu¹, Min Zhou¹, Lin Ma¹, Min Zhang¹

Affiliation

¹ School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, China.

PMID: 39807970
DOI: 10.1021/acs.joc.4c02855

Abstract

A highly efficient Minisci reaction of pyrimidines with alkyl radical generated from visible-light-induced activation of simple C(sp³)-H feedstocks such as (cyclo)alkanes, ethers, alcohols, esters, and amides is reported. A mechanistic study revealed that alkyl radical was generated via hydrogen atom transfer (HAT) of C(sp³)-H with dichloromethyl radical (·CHCl₂), which was generated by photoreduction of chloroform.