Synthesis 2022; 54(05): 1353-1364
DOI: 10.1055/a-1674-6564
paper

Cobalt-Catalyzed Hydroxyperfluoroalkylation of Alkenes with Perfluoroalkyl Bromides and Atmospheric Oxygen

Qilin Sun
a   Department of Applied Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China
,
Liangzhi Pang
a   Department of Applied Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China
,
Shuxian Mao
a   Department of Applied Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China
,
Wu Fan
b   Key Laboratory of Tobacco Flavor Basic Research, Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou 450001, P. R. of China
,
Yuyi Zhou
c   School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, P. R. of China
,
Jing Xu
c   School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, P. R. of China
,
Suhua Li
c   School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, P. R. of China
d   Key Lab of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510641, P. R. of China
,
Qiankun Li
a   Department of Applied Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China
› Author Affiliations
We would like to thank the National Natural Science Foundation of China (Grant 22001008 to Q.L., 21971260 to S.L.), the Natural Science Foundation of Anhui Province (Grant 2008085QB61) and Anhui Agricultural University (RC381902, 2019zd13) to Q.L., Natural Science Foundation of Guangdong Province for Distinguished Young Scholars (2018B030306018), the Program for Guangdong Introducing Innovative and Entrepreneurial Teams (2017ZT07C069), the Pearl River Talent Recruitment Program of Guangdong Province (2019QN01L111) and the Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology (No. 2018kf04) to S.L., Innovation Projects of Zhengzhou Tobacco Research Institute (442020CR0320 to W.F.).


Abstract

A mild and efficient method for the cobalt-catalyzed hydroxyperfluoroalkylation of alkenes has been developed. This method demonstrated broad substrate scope, good yields, and mild conditions with the tolerance of mono-, di-, and trisubstituted alkenes including both styrenes and non-activated aliphatic olefins. This strategy offered a valuable solution for rapid and efficient construction of β-perfluoro­alkyl alcohols using widely available and inexpensive perfluoroalkyl bromides­ and atmospheric oxygen.

Supporting Information



Publication History

Received: 27 September 2021

Accepted after revision: 20 October 2021

Accepted Manuscript online:
20 October 2021

Article published online:
22 November 2021

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