Literature DB >> 24030756

Synthesis of gem-difluorocyclopropa(e)nes and O-, S-, N-, and P-difluoromethylated compounds with TMSCF(2)Br.

Lingchun Li1, Fei Wang, Chuanfa Ni, Jinbo Hu.   

Abstract

Two-in-one: Me3 SiCF2 Br is an efficient difluorocarbene source and is compatible with both neutral and aqueous basic conditions. Bromide-ion-initiated [2+1] cycloaddition with alkenes/alkynes and hydroxide ion promoted α-addition with (thio)phenols, (thio)alcohols, sulfinates, heterocyclic amines, and H-phosphine oxides give the corresponding gem-difluorinated compounds with broad functional-group tolerance.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbenes; cycloaddition; fluorine; heterocycles; synthetic methods

Year:  2013        PMID： 24030756     DOI： 10.1002/anie.201306703

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


  10 in total

Review 1.  Synthesis of Tri- and Difluoromethoxylated Compounds by Visible-Light Photoredox Catalysis.

Authors:  Johnny W Lee; Katarzyna N Lee; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-28       Impact factor: 15.336

2.  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

3.  Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine.

Authors:  Fei Wang; Lingchun Li; Chuanfa Ni; Jinbo Hu
Journal:  Beilstein J Org Chem       Date:  2014-02-06       Impact factor: 2.883

4.  Deoxyfluorination of alcohols with 3,3-difluoro-1,2-diarylcyclopropenes.

Authors:  Lingchun Li; Chuanfa Ni; Fei Wang; Jinbo Hu
Journal:  Nat Commun       Date:  2016-11-14       Impact factor: 14.919

5.  Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers.

Authors:  Vyacheslav I Supranovich; Vitalij V Levin; Alexander D Dilman
Journal:  Beilstein J Org Chem       Date:  2020-06-29       Impact factor: 2.883

6.  Total Synthesis of the Antimycobacterial Natural Product Chlorflavonin and Analogs via a Late-Stage Ruthenium(II)-Catalyzed ortho-C(sp2)-H-Hydroxylation.

Authors:  Alexander Berger; Talea Knak; Anna-Lene Kiffe-Delf; Korana Mudrovcic; Vinayak Singh; Mathew Njoroge; Bjoern B Burckhardt; Mohanraj Gopalswamy; Beate Lungerich; Lutz Ackermann; Holger Gohlke; Kelly Chibale; Rainer Kalscheuer; Thomas Kurz
Journal:  Pharmaceuticals (Basel)       Date:  2022-08-10

7.  Discovery of a synthesis method for a difluoroglycine derivative based on a path generated by quantum chemical calculations.

Authors:  Tsuyoshi Mita; Yu Harabuchi; Satoshi Maeda
Journal:  Chem Sci       Date:  2020-05-22       Impact factor: 9.825

8.  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

9.  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

10.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825
  10 in total

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