Literature DB >> 12762751

Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones.

G K Surya Prakash1, Jinbo Hu, George A Olah.   

Abstract

A new and efficient method for the preparation of tri- and difluoromethylsilanes using magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes is reported using tri- and difluoromethyl sulfides, sulfoxides, and sulfones. The byproduct of the process is diphenyl disulfide. Since phenyl trifluoromethyl sulfone, sulfoxide, and sulfide are readily prepared from trifluoromethane (CF(3)H) and diphenyl disulfide, the method can be considered to be catalytic in diphenyl disulfide for the preparation of (trifluoromethyl)trimethylsilane (TMS-CF(3)) from non-ozone-depleting trifluoromethane.

Entities:  

Year:  2003        PMID: 12762751     DOI: 10.1021/jo030110z

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Alpha-fluoro-alpha-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: efficient stereoselective Michael addition to chalcones.

Authors:  G K Surya Prakash; Fang Wang; Timothy Stewart; Thomas Mathew; George A Olah
Journal:  Proc Natl Acad Sci U S A       Date:  2009-02-23       Impact factor: 11.205

2.  Copper-mediated difluoromethylation of aryl and vinyl iodides.

Authors:  Patrick S Fier; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-03-14       Impact factor: 15.419

3.  Chlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium.

Authors:  Zhang Feng; Qiao-Qiao Min; Xia-Ping Fu; Lun An; Xingang Zhang
Journal:  Nat Chem       Date:  2017-03-14       Impact factor: 24.427

4.  Nucleophilic difluoromethylation and difluoromethylenation of aldehydes and ketones using diethyl difluoromethylphosphonate.

Authors:  Petr Beier; Anastasia V Alexandrova; Mikhail Zibinsky; G K Surya Prakash
Journal:  Tetrahedron       Date:  2008-12       Impact factor: 2.457

5.  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

6.  Efficient 1,4-addition of alpha-substituted fluoro(phenylsulfonyl)methane derivatives to alpha,beta-unsaturated compounds.

Authors:  G K Surya Prakash; Xiaoming Zhao; Sujith Chacko; Fang Wang; Habiba Vaghoo; George A Olah
Journal:  Beilstein J Org Chem       Date:  2008-05-21       Impact factor: 2.883

  6 in total

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