Literature DB >> 25766315

Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ.

Bilguun Bayarmagnai1, Christian Matheis, Kévin Jouvin, Lukas J Goossen.   

Abstract

A copper-CF2 H complex generated in situ from copper thiocyanate and TMSCF2 H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts. This strategy enables the introduction of difluoromethylthio groups-a largely unexplored substituent with highly promising properties-into drug-like molecules.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Sandmeyer reaction; copper; difluoromethylthiolation; fluorine; synthetic methods

Mesh:

Substances:

Year:  2015        PMID: 25766315     DOI: 10.1002/anie.201500899

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


  7 in total

Review 1.  Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F).

Authors:  Louise Ruyet; Tatiana Besset
Journal:  Beilstein J Org Chem       Date:  2020-05-18       Impact factor: 2.883

2.  Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions.

Authors:  Qing Huang; Xiangjun Peng; Hong Li; Haiping He; Liangxian Liu
Journal:  Molecules       Date:  2022-01-25       Impact factor: 4.411

3.  Mild, Organo-Catalysed Borono-Deamination as a Key to Late-Stage Pharmaceutical Precursors and 18F-Labelled Radiotracers.

Authors:  Raúl M Pérez-García; Patrick J Riss
Journal:  Front Chem       Date:  2022-04-26       Impact factor: 5.545

4.  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

5.  Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides.

Authors:  Jiang Wu; Yafei Liu; Changhui Lu; Qilong Shen
Journal:  Chem Sci       Date:  2016-02-17       Impact factor: 9.825

6.  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

7.  Pd-Catalyzed Directed Thiocyanation Reaction by C-H Bond Activation.

Authors:  Mélissa Gao; Mu-Yi Chen; Xavier Pannecoucke; Philippe Jubault; Tatiana Besset
Journal:  Chemistry       Date:  2020-11-03       Impact factor: 5.236

  7 in total

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