Copper-Catalyzed Radical 1,2-Carbotrifluoromethylselenolation of Alkenes under Ambient Conditions

Jiao Yu; Ning-Yuan Yang; Jiang-Tao Cheng; Tian-Ya Zhan; Cheng Luan; Liu Ye; Qiang-Shuai Gu; Zhong-Liang Li; Guo-Qiang Chen; Xin-Yuan Liu

doi:10.1021/acs.orglett.1c00436

Copper-Catalyzed Radical 1,2-Carbotrifluoromethylselenolation of Alkenes under Ambient Conditions

Org Lett. 2021 Mar 5;23(5):1945-1949. doi: 10.1021/acs.orglett.1c00436. Epub 2021 Feb 24.

Authors

Jiao Yu^{1

2

3}, Ning-Yuan Yang³, Jiang-Tao Cheng³, Tian-Ya Zhan³, Cheng Luan³, Liu Ye⁴, Qiang-Shuai Gu⁴, Zhong-Liang Li⁴, Guo-Qiang Chen¹, Xin-Yuan Liu³

Affiliations

¹ College of Chemistry and Environmental Engineering, Shenzhen University, 1066 Xueyuan Road, Shenzhen 518071, China.
² College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
³ Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.
⁴ Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.

PMID: 33625234
DOI: 10.1021/acs.orglett.1c00436

Abstract

We have described a copper-catalyzed radical 1,2-carbotrifluoromethylselenolation of alkenes using the readily available alkyl halides and (Me₄N)SeCF₃ salt. Critical to the success is the use of a proline-based N,N,P-ligand to enhance the reducing capability of copper for easy conversion of diverse alkyl halides to the corresponding radicals via a single-electron transfer process. The reaction features a broad substrate scope, including various mono-, di-, and trisubstituted alkenes with many functional groups.