Literature DB >> 33488833

Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols.

Armin Ariamajd1, Nils J Gerwien1, Benjamin Schwabe1, Stefan Dix1, Matthew N Hopkinson1.   

Abstract

A series of 2-(perfluoroalkylthio)benzothiazolium (BT-SRF) salts have been synthesized that serve as convenient sources of hitherto underexplored perfluoroalkylthiolate anions. An investigation of their reactivity in a deoxygenative nucleophilic substitution reaction led to the development of an unprecedented process that provides pentafluoroethyl and heptafluoropropyl thioethers directly from readily available alcohols.
Copyright © 2021, Ariamajd et al.; licensee Beilstein-Institut.

Entities:  

Keywords:  alcohols; benzothiazolium salts; deoxygenative reactions; fluorine; perfluoroalkylthiolation; thioethers

Year:  2021        PMID： 33488833      PMCID： PMC7801780          DOI： 10.3762/bjoc.17.8

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN： 1860-5397            Impact factor:   2.883


  21 in total

Review 1.  Use of ArSO2SRf reagents: an efficient tool for the introduction of SRf moieties.

Authors:  Xavier Pannecoucke; Tatiana Besset
Journal:  Org Biomol Chem       Date:  2019-02-13       Impact factor: 3.876

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

Authors:  Lvqi Jiang; Jinlong Qian; Wenbin Yi; Guoping Lu; Chun Cai; Wei Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-16       Impact factor: 15.336

Review 3.  Synthetic methods for compounds having CF3-S units on carbon by trifluoromethylation, trifluoromethylthiolation, triflylation, and related reactions.

Authors:  Xiu-Hua Xu; Kohei Matsuzaki; Norio Shibata
Journal:  Chem Rev       Date:  2014-08-14       Impact factor: 60.622

Review 4.  Late stage trifluoromethylthiolation strategies for organic compounds.

Authors:  Sebastian Barata-Vallejo; Sergio Bonesi; Al Postigo
Journal:  Org Biomol Chem       Date:  2016-07-26       Impact factor: 3.876

5.  Perfluoroalkylation of Thiosulfonates: Synthesis of Perfluoroalkyl Sulfides.

Authors:  Ziwei Luo; Xinkan Yang; Gavin Chit Tsui
Journal:  Org Lett       Date:  2020-07-10       Impact factor: 6.005

6.  Cupration of C2F5H: isolation, structure, and synthetic applications of [K(DMF)2][(t-BuO)Cu(C2F5)]. Highly efficient pentafluoroethylation of unactivated aryl bromides.

Authors:  Anton Lishchynskyi; Vladimir V Grushin
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

Review 7.  Liquid crystals based on fluorinated carbohydrates.

Authors:  R Miethchen; M Hein
Journal:  Carbohydr Res       Date:  2000-07-10       Impact factor: 2.104

Review 8.  Applications of Fluorine in Medicinal Chemistry.

Authors:  Eric P Gillis; Kyle J Eastman; Matthew D Hill; David J Donnelly; Nicholas A Meanwell
Journal:  J Med Chem       Date:  2015-07-22       Impact factor: 7.446

9.  Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation.

Authors:  Vladimir N Boiko
Journal:  Beilstein J Org Chem       Date:  2010-08-18       Impact factor: 2.883

Review 10.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622
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  2 in total

Review 1.  Recent trends in dehydroxylative trifluoro-methylation, -methoxylation, -methylthiolation, and -methylselenylation of alcohols.

Authors:  Yan Cao; Roya Ahmadi; Mohammad Reza Poor Heravi; Alibek Issakhov; Abdol Ghaffar Ebadi; Esmail Vessally
Journal:  RSC Adv       Date:  2021-12-13       Impact factor: 4.036

2.  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
  2 in total

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