Literature DB >> 26474170

Direct Trifluoromethylthiolation and Perfluoroalkylthiolation of C(sp(2))-H Bonds with CF3SO2Na and RfSO2Na.

Lvqi Jiang1, Jinlong Qian1, Wenbin Yi2, Guoping Lu1, Chun Cai1, Wei Zhang3.   

Abstract

A new method for CF3SO2Na-based direct trifluoromethylthiolation of C(sp(2))-H bonds has been developed. CF3SSCF3 is generated in situ from cheap and easy-to-handle CF3SO2Na, and in the presence of CuCl can be used for electrophilic trifluoromethylthiolation of indoles, pyrroles, and enamines. The method has been extended to perfluoroalkylthiolation reactions using RfSO2Na.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; fluorine; heterocycles; sulfur; synthetic methods

Year:  2015        PMID： 26474170     DOI： 10.1002/anie.201508495

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  12 in total

1.  Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by PIII /PV =O Redox Cycling.

Authors:  Avipsa Ghosh; Morgan Lecomte; Shin-Ho Kim-Lee; Alexander T Radosevich
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-25       Impact factor: 15.336

Review 2.  Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Authors:  Raju Jannapu Reddy; Arram Haritha Kumari
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

3.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na.

Authors:  Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2017-12-19       Impact factor: 2.883

4.  Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines.

Authors:  Alejandra Riesco-Domínguez; Jeroen van de Wiel; Trevor A Hamlin; Bas van Beek; Stephen D Lindell; Daniel Blanco-Ania; F Matthias Bickelhaupt; Floris P J T Rutjes
Journal:  J Org Chem       Date:  2018-01-30       Impact factor: 4.354

5.  Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols.

Authors:  Armin Ariamajd; Nils J Gerwien; Benjamin Schwabe; Stefan Dix; Matthew N Hopkinson
Journal:  Beilstein J Org Chem       Date:  2021-01-08       Impact factor: 2.883

6.  Photoinduced C(sp3)-H sulfination empowers the direct and chemoselective introduction of the sulfonyl group.

Authors:  Shengfei Jin; Graham C Haug; Ramon Trevino; Viet D Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2021-09-28       Impact factor: 9.825

7.  Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation.

Authors:  Vu T Nguyen; Graham C Haug; Viet D Nguyen; Ngan T H Vuong; Guna B Karki; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2022-03-21       Impact factor: 9.825

8.  Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis.

Authors:  Sadayuki Arimori; Okiya Matsubara; Masahiro Takada; Motoo Shiro; Norio Shibata
Journal:  R Soc Open Sci       Date:  2016-05-25       Impact factor: 2.963

9.  2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions.

Authors:  Zhongyan Huang; Kenta Okuyama; Chen Wang; Etsuko Tokunaga; Xiaorui Li; Norio Shibata
Journal:  ChemistryOpen       Date:  2016-01-28       Impact factor: 2.911

10.  Late-stage trifluoromethylthiolation of benzylic C-H bonds.

Authors:  Wentao Xu; Wenliang Wang; Tao Liu; Jin Xie; Chengjian Zhu
Journal:  Nat Commun       Date:  2019-10-25       Impact factor: 14.919
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