HCF2Se/HCF2S Installation by Tandem Substitutions from Alkyl Bromides

Min Zhang; Jin-Hong Lin; Ji-Chang Xiao

doi:10.1021/acs.joc.1c01718

HCF₂Se/HCF₂S Installation by Tandem Substitutions from Alkyl Bromides

J Org Chem. 2021 Sep 17;86(18):13153-13159. doi: 10.1021/acs.joc.1c01718. Epub 2021 Sep 3.

Authors

Min Zhang¹, Jin-Hong Lin^{1

2}, Ji-Chang Xiao¹

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
² Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China.

PMID: 34476948
DOI: 10.1021/acs.joc.1c01718

Abstract

Herein we describe an efficient construction of HCF₂Se and HCF₂S groups by tandem substitutions between alkyl bromides and a reagent system consisting of MSeCN (or MSCN) and Ph₃P⁺CF₂H Br^-. The tandem process occurs via the first nucleophilic substitution of alkyl bromides by -SeCN (or -SCN) and the subsequent nucleophilic difluoromethylation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bromides*
Indicators and Reagents

Substances

Bromides
Indicators and Reagents