Photoinduced Copper-Catalyzed C(sp3)-P Bond Formation by Coupling of Secondary Phosphines with N-(Acyloxy)phthalimides and N-Fluorocarboxamides

Chuanyong Wang; Qiangqiang Ge; Cheng Xu; Zhongqiu Xing; Jianqi Xiong; Yu Zheng; Wei-Liang Duan

doi:10.1021/acs.orglett.3c00475

Photoinduced Copper-Catalyzed C(sp³)-P Bond Formation by Coupling of Secondary Phosphines with N-(Acyloxy)phthalimides and N-Fluorocarboxamides

Org Lett. 2023 Mar 10;25(9):1583-1588. doi: 10.1021/acs.orglett.3c00475. Epub 2023 Feb 24.

Authors

Chuanyong Wang¹, Qiangqiang Ge¹, Cheng Xu¹, Zhongqiu Xing¹, Jianqi Xiong¹, Yu Zheng², Wei-Liang Duan^{1

3}

Affiliations

¹ College of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, Yangzhou 225002, China.
² Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
³ School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an 710119, China.

PMID: 36826372
DOI: 10.1021/acs.orglett.3c00475

Abstract

A photoinduced copper-catalyzed C(sp³)-P bond formation has been developed by using N-(acyloxy)phthalimides as radical precursors and secondary phosphine boranes as coupling partners. A variety of alkyl carboxylic acid derivatives can be readily transformed into the corresponding phosphines with high reaction efficiency and structural diversity. Besides, utilizing the 1,5-HAT of the N-centered radical process, the δ C(sp³)-H bond can be coupled with secondary phosphines, which provides a novel method for the regioselective formation of C(sp³)-P bonds.