Literature DB >> 27379404

Trifluoromethylthiolation and Trifluoromethylselenolation of α-Diazo Esters Catalyzed by Copper.

Christian Matheis1, Thilo Krause1, Valentina Bragoni1, Lukas J Goossen2.   

Abstract

α-Diazo esters are smoothly converted into the corresponding trifluoromethyl thio- or selenoethers by reaction with Me4 NSCF3 or Me4 NSeCF3 , respectively, in the presence of catalytic amounts of copper thiocyanate. This straightforward method gives high yields under neutral conditions at room temperature and is applicable to a wide range of functionalized molecules, including diverse α-amino acid derivatives. It is well-suited for the late-stage introduction of trifluoromethylthio or -seleno groups into drug-like molecules.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; diazo compounds; fluorine; fluoroalkylthiolation; synthetic methods

Year:  2016        PMID: 27379404     DOI: 10.1002/chem.201602730

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  5 in total

1.  Electrophilic trifluoromethylselenolation of terminal alkynes with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate.

Authors:  Clément Ghiazza; Anis Tlili; Thierry Billard
Journal:  Beilstein J Org Chem       Date:  2017-12-07       Impact factor: 2.883

2.  Electrophilic Trifluoromethylselenolation of Boronic Acids.

Authors:  Clément Ghiazza; Anis Tlili; Thierry Billard
Journal:  Molecules       Date:  2017-05-19       Impact factor: 4.411

Review 3.  Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

Authors:  Xiaowei Li; Xiaolin Shi; Xiangqian Li; Dayong Shi
Journal:  Beilstein J Org Chem       Date:  2019-09-23       Impact factor: 2.883

Review 4.  Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions.

Authors:  Clément Ghiazza; Anis Tlili
Journal:  Beilstein J Org Chem       Date:  2020-03-03       Impact factor: 2.883

5.  Markovnikov-Type Hydrotrifluoromethylchalcogenation of Unactivated Terminal Alkenes with [Me4N][XCF3] (X = S, Se) and TfOH.

Authors:  Jin Shi; Cheng-Pan Zhang
Journal:  Molecules       Date:  2020-10-03       Impact factor: 4.411

  5 in total

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