Huang Haoran, Lin Xiaoyu, Yang Fanyuanhang, Ren Yuxi, Gao Yuzhen, Su Weiping
State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
Org Lett. 2024 Dec 27;26(51):11195-11200. doi: 10.1021/acs.orglett.4c04294. Epub 2024 Dec 13.
The direct carboxylation of C(sp)-H bonds with CO represents a challenging but highly attractive strategy in organic synthesis. In this study, we presented a visible-light-catalyzed strategy for carboxylating remote C(sp)-H bonds with CO via aryl radical induced 1,5-hydrogen atom transfer. This transformation involves generating alkyl radicals via 1,5-hydrogen atom transfer from aryl radicals, forming alkyl carbanions as key intermediates, and a subsequent nucleophilic attack with CO, thereby enabling access to a variety of tertiary and quaternary carboxylic acids in moderate to good yields.