Controllable Double Difluoromethylene Insertions into S−Cu Bonds: (Arylthio)tetrafluoroethylation of Aryl Iodides with TMSCF<sub>2</sub>Br-Reference-Cited by-同舟云学术

Controllable Double Difluoromethylene Insertions into S−Cu Bonds: (Arylthio)tetrafluoroethylation of Aryl Iodides with TMSCF₂Br

Published:2024-03-04 Issue:14 Volume:63 Page:
ISSN:1433-7851
Container-title:Angewandte Chemie International Edition
language:en
Short-container-title:Angew Chem Int Ed

Author:

Pan Shitao¹,Xie Qiqiang¹,Wang Xiu¹,Huang Rumin¹,Lu Yuhao¹,Ni Chuanfa¹,Hu Jinbo¹^ORCID

Affiliation:

1. Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Ling-Ling Road Shanghai 200032 China

Abstract

AbstractA new method of constructing “ArSCF2CF2Cu” from ArSCu and TMSCF2Br (TMS=trimethylsilyl) has been developed. The cross‐coupling reactions of the obtained “ArSCF2CF2Cu” with diverse aryl iodides (Ar′I) provide an efficient access to Ar′CF2CF2SAr. Mechanistic studies demonstrate that the “ArSCF2CF2Cu” species were generated through controllable double difluoromethylene insertions into ArS−Cu bonds rather than the 1,2‐addition of ArSCu to tetrafluoroethylene.

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202400839

Reference148 articles.

1. For examples see:

2. Stereoselective addition of CF3SiMe3 on azirines. Synthesis of (E)-aziridines

3. Preparation of Tri- and Difluoromethylated Amines from Aldimines Using (Trifluoromethyl)trimethylsilane

4. Trifluoromethylation of non-activated aldimines with trimethyl(trifluoromethyl)silane in the presence of tetramethylammonium fluoride: A closer look into the reaction route

5. Nucleophilic Trifluoromethylation of Imines under Acidic Conditions