Literature DB >> 25420412

Direct dehydroxytrifluoromethylthiolation of alcohols using silver(I) trifluoromethanethiolate and tetra-n-butylammonium iodide.

Jian-Bo Liu1, Xiu-Hua Xu, Zeng-Hao Chen, Feng-Ling Qing.   

Abstract

An unprecedented reaction for the direct trifluoromethylthiolation and fluorination of alkyl alcohols using AgSCF3 and nBu4NI has been developed. The trifluoromethylthiolated compounds and alkyl fluorides were selectively formed by changing the ratio of AgSCF3/nBu4NI. This protocol is tolerant of different functional groups and might be applicable to late-stage trifluoromethylthiolation of alcohols.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alcohols; chemoselectivity; fluorine; silver; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 25420412     DOI： 10.1002/anie.201409983

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


  8 in total

1.  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

2.  Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Authors:  Yong Li; Zhishi Ye; Tabitha M Bellman; Teng Chi; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.072

3.  When Weaker Can Be Tougher: The Role of Oxidation State (I) in P- vs N-Ligand-Derived Ni-Catalyzed Trifluoromethylthiolation of Aryl Halides.

Authors:  Indrek Kalvet; Qianqian Guo; Graham J Tizzard; Franziska Schoenebeck
Journal:  ACS Catal       Date:  2017-01-31       Impact factor: 13.084

4.  Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me4 N)SCF3.

Authors:  Thomas Scattolin; Kristina Deckers; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-09       Impact factor: 15.336

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.  Electrophilic Reagents for the Direct Incorporation of Uncommon SCF2CF2H and SCF2CF3 Motifs.

Authors:  Jordi Mestre; Miguel Bernús; Sergio Castillón; Omar Boutureira
Journal:  J Org Chem       Date:  2022-08-09       Impact factor: 4.198

7.  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

8.  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
  8 in total

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