Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes

Lvqi Jiang; Tianqi Ding; Wen Bin Yi; Xin Zeng; Wei Zhang

doi:10.1021/acs.orglett.8b00581

Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes

Lvqi Jiang
, Tianqi Ding
, Wen Bin Yi
, Xin Zeng
, Wei Zhang

Chemistry

Nanjing University of Science and Technology

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

Abstract

The unprecedented use of CF₃SO₂Cl for direct bifunctional chloro-trifluoromethylthiolation of alkenes and alkynes is reported. CF₃SCl, which is generated by the reduction of PPh₃, undergoes electrophilic addition and then chlorination to give the bifunctionalized products without using an additional chlorine source. The method is also applicable for chloro-difluoromethylthiolation using CF₂HSO₂Cl.

Original language	English
Pages (from-to)	2236-2240
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.8b00581
State	Published - Apr 20 2018

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b00581

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title = "Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes",

abstract = "The unprecedented use of CF3SO2Cl for direct bifunctional chloro-trifluoromethylthiolation of alkenes and alkynes is reported. CF3SCl, which is generated by the reduction of PPh3, undergoes electrophilic addition and then chlorination to give the bifunctionalized products without using an additional chlorine source. The method is also applicable for chloro-difluoromethylthiolation using CF2HSO2Cl.",

author = "Lvqi Jiang and Tianqi Ding and Yi, \{Wen Bin\} and Xin Zeng and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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day = "20",

doi = "10.1021/acs.orglett.8b00581",

language = "English",

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journal = "Organic Letters",

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T1 - Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes

AU - Jiang, Lvqi

AU - Ding, Tianqi

AU - Yi, Wen Bin

AU - Zeng, Xin

AU - Zhang, Wei

PY - 2018/4/20

Y1 - 2018/4/20

N2 - The unprecedented use of CF3SO2Cl for direct bifunctional chloro-trifluoromethylthiolation of alkenes and alkynes is reported. CF3SCl, which is generated by the reduction of PPh3, undergoes electrophilic addition and then chlorination to give the bifunctionalized products without using an additional chlorine source. The method is also applicable for chloro-difluoromethylthiolation using CF2HSO2Cl.

AB - The unprecedented use of CF3SO2Cl for direct bifunctional chloro-trifluoromethylthiolation of alkenes and alkynes is reported. CF3SCl, which is generated by the reduction of PPh3, undergoes electrophilic addition and then chlorination to give the bifunctionalized products without using an additional chlorine source. The method is also applicable for chloro-difluoromethylthiolation using CF2HSO2Cl.

UR - https://www.scopus.com/pages/publications/85045894262

UR - https://www.scopus.com/pages/publications/85045894262#tab=citedBy

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DO - 10.1021/acs.orglett.8b00581

M3 - Article

C2 - 29624070

AN - SCOPUS:85045894262

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes

Abstract

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