Literature DB >> 27306975

Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H.

Joseph L Howard1, Christiane Schotten1, Stephen T Alston1, Duncan L Browne1.   

Abstract

We report an operationally simple, metal-free approach for the late-stage introduction of the important lipophilic hydrogen-bond donor motif, SCF2H. This reaction converts diaryl- and dialkyl-disulfides into the corresponding aryl/alkyl-SCF2H through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. This method is notable for its use of commercially available TMSCF2H, and does not rely on the need for handling of sensitive metal complexes.

Entities:  

Year:  2016        PMID: 27306975     DOI: 10.1039/c6cc02693a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  4 in total

1.  Diaryl disulfides and thiosulfonates as combretastatin A-4 analogues: Synthesis, cytotoxicity and antitubulin activity.

Authors:  Rejane Gonçalves Diniz Khodyuk; Ruoli Bai; Ernest Hamel; Estela Mariana Guimarães Lourenço; Euzébio Guimarães Barbosa; Adilson Beatriz; Edson Dos Anjos Dos Santos; Dênis Pires de Lima
Journal:  Bioorg Chem       Date:  2020-06-15       Impact factor: 5.307

2.  One-pot multistep mechanochemical synthesis of fluorinated pyrazolones.

Authors:  Joseph L Howard; William Nicholson; Yerbol Sagatov; Duncan L Browne
Journal:  Beilstein J Org Chem       Date:  2017-09-14       Impact factor: 2.883

3.  Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-).

Authors:  Jacek Pecyna; Igor Rončević; Josef Michl
Journal:  Molecules       Date:  2019-10-21       Impact factor: 4.411

4.  Radical difluoromethylthiolation of aromatics enabled by visible light.

Authors:  Jianbin Li; Dianhu Zhu; Leiyang Lv; Chao-Jun Li
Journal:  Chem Sci       Date:  2018-06-01       Impact factor: 9.825

  4 in total

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