Metal-Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane- sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro- alkanesulfinate

Qiang Yan; Lvqi Jiang; Wenbin Yi; Qiran Liu; Wei Zhang

doi:10.1002/adsc.201700270

Metal-Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane- sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro- alkanesulfinate

Qiang Yan
, Lvqi Jiang
, Wenbin Yi
, Qiran Liu
, Wei Zhang

Chemistry

Nanjing University of Science and Technology

Research output: Contribution to journal › Article › peer-review

Abstract

A method for direct difluoromethylthiolation of Ar−H bonds is introduced. The stable and easy-to-handle HCF₂SO₂Na is reduced with (EtO)₂P(O)H in the presence of TMSCl to generate HCF₂S⁺ for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF₃SO₂Na and the perfluoroalkylthiolation with R_fSO₂Na of arenes and heteroarenes. Reaction mechanisms associated with the metal-free electrophilic fluoroalkylthiolation reactions are also discussed. (Figure presented.).

Original language	English
Pages (from-to)	2471-2480
Number of pages	10
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	14
DOIs	https://doi.org/10.1002/adsc.201700270
State	Published - Jul 17 2017

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

difluoromethylthiolation
metal catalyst-free conditions
perfluoroalkylthiolation
trifluoromethylthiolation

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10.1002/adsc.201700270

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Metal-Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane- sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro- alkanesulfinate. / Yan, Qiang; Jiang, Lvqi; Yi, Wenbin et al.
In: Advanced Synthesis and Catalysis, Vol. 359, No. 14, 17.07.2017, p. 2471-2480.

Research output: Contribution to journal › Article › peer-review

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title = "Metal-Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane- sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro- alkanesulfinate",

abstract = "A method for direct difluoromethylthiolation of Ar−H bonds is introduced. The stable and easy-to-handle HCF2SO2Na is reduced with (EtO)2P(O)H in the presence of TMSCl to generate HCF2S+ for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF3SO2Na and the perfluoroalkylthiolation with RfSO2Na of arenes and heteroarenes. Reaction mechanisms associated with the metal-free electrophilic fluoroalkylthiolation reactions are also discussed. (Figure presented.).",

keywords = "difluoromethylthiolation, metal catalyst-free conditions, perfluoroalkylthiolation, trifluoromethylthiolation",

author = "Qiang Yan and Lvqi Jiang and Wenbin Yi and Qiran Liu and Wei Zhang",

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AU - Yan, Qiang

AU - Jiang, Lvqi

AU - Yi, Wenbin

AU - Liu, Qiran

AU - Zhang, Wei

PY - 2017/7/17

Y1 - 2017/7/17

N2 - A method for direct difluoromethylthiolation of Ar−H bonds is introduced. The stable and easy-to-handle HCF2SO2Na is reduced with (EtO)2P(O)H in the presence of TMSCl to generate HCF2S+ for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF3SO2Na and the perfluoroalkylthiolation with RfSO2Na of arenes and heteroarenes. Reaction mechanisms associated with the metal-free electrophilic fluoroalkylthiolation reactions are also discussed. (Figure presented.).

AB - A method for direct difluoromethylthiolation of Ar−H bonds is introduced. The stable and easy-to-handle HCF2SO2Na is reduced with (EtO)2P(O)H in the presence of TMSCl to generate HCF2S+ for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF3SO2Na and the perfluoroalkylthiolation with RfSO2Na of arenes and heteroarenes. Reaction mechanisms associated with the metal-free electrophilic fluoroalkylthiolation reactions are also discussed. (Figure presented.).

KW - difluoromethylthiolation

KW - metal catalyst-free conditions

KW - perfluoroalkylthiolation

KW - trifluoromethylthiolation

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Metal-Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane- sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro- alkanesulfinate

Abstract

ASJC Scopus Subject Areas

Keywords

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