Literature DB >> 25707945

Direct trifluoromethylthiolation of unactivated C(sp(3))-H using silver(I) trifluoromethanethiolate and potassium persulfate.

Hao Wu1, Zhiwei Xiao, Junhui Wu, Yong Guo, Ji-Chang Xiao, Chao Liu, Qing-Yun Chen.   

Abstract

A practical and efficient method for the direct trifluoromethylthiolation of unactivated C(sp(3) )H bonds by AgSCF3 /K2 S2 O8 under mild conditions is described. The reaction has a good functional-group tolerance and good selectivity. Initial mechanistic investigations indicate that the reaction may involve a radical process in which K2 S2 O8 plays key roles in both the activation of the C(sp(3) )H bond and the oxidation of AgSCF3 .
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; fluorine; radical reactions; synthetic methods; trifluoromethylthiolation

Mesh：

Substances：

Year:  2015        PMID： 25707945     DOI： 10.1002/anie.201411953

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


  11 in total

1.  Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate.

Authors:  Melissa Lee; Melanie S Sanford
Journal:  Org Lett       Date:  2017-01-17       Impact factor: 6.005

2.  Copper-Catalyzed, N-Directed Csp3-H Trifluoromethylthiolation (-SCF3) and Trifluoromethylselenation (-SeCF3).

Authors:  Atanu Modak; Emily N Pinter; Silas P Cook
Journal:  J Am Chem Soc       Date:  2019-11-07       Impact factor: 15.419

3.  Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers.

Authors:  Jian He; Caiyou Chen; Gregory C Fu; Jonas C Peters
Journal:  ACS Catal       Date:  2018-10-31       Impact factor: 13.084

4.  Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

Authors:  Jian Zheng; Lu Wang; Jin-Hong Lin; Ji-Chang Xiao; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-21       Impact factor: 15.336

5.  Diversification of aliphatic C-H bonds in small molecules and polyolefins through radical chain transfer.

Authors:  Timothy J Fazekas; Jill W Alty; Eliza K Neidhart; Austin S Miller; Frank A Leibfarth; Erik J Alexanian
Journal:  Science       Date:  2022-02-03       Impact factor: 63.714

6.  Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes.

Authors:  Xiaojuan Li; Qiang Zhang; Weigang Zhang; Jinzhu Ma; Yi Wang; Yi Pan
Journal:  Beilstein J Org Chem       Date:  2021-02-24       Impact factor: 2.883

7.  Intermolecular CDC amination of remote and proximal unactivated Csp3 -H bonds through intrinsic substrate reactivity - expanding towards a traceless directing group.

Authors:  Suresh Rajamanickam; Mayank Saraswat; Sugumar Venkataramani; Bhisma K Patel
Journal:  Chem Sci       Date:  2021-10-27       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.  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

10.  Deoxygenative trifluoromethylthiolation of carboxylic acids.

Authors:  Runze Mao; Srikrishna Bera; Alexis Cheseaux; Xile Hu
Journal:  Chem Sci       Date:  2019-08-26       Impact factor: 9.825
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