Literature DB >> 24308287

Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides.

Benjamin N Rocke1, Kevin B Bahnck, Michael Herr, Sophie Lavergne, Vincent Mascitti, Christian Perreault, Jana Polivkova, Andrei Shavnya.   

Abstract

Organozinc reagents react with the SO2 surrogate DABSO, and the resulting zinc sulfinate salts are alkylated in situ to afford sulfones. This transformation has a broad scope and is compatible with a wide range of structural motifs of medicinal chemistry relevance including nitrile, secondary carbamates, and nitrogen-containing heterocycles.

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Year:  2013        PMID： 24308287     DOI： 10.1021/ol4031233

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

Review 2.  Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry.

Authors:  Minghao Feng; Bingqing Tang; Steven H Liang; Xuefeng Jiang
Journal:  Curr Top Med Chem       Date:  2016       Impact factor: 3.295

3.  Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: a gas- and reductant-free process.

Authors:  Edward J Emmett; Barry R Hayter; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-27       Impact factor: 15.336

4.  Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.

Authors:  James R Colombe; J Robb DeBergh; Stephen L Buchwald
Journal:  Org Lett       Date:  2015-06-11       Impact factor: 6.005

5.  C-H methylation of heteroarenes inspired by radical SAM methyl transferase.

Authors:  Jinghan Gui; Qianghui Zhou; Chung-Mao Pan; Yuki Yabe; Aaron C Burns; Michael R Collins; Martha A Ornelas; Yoshihiro Ishihara; Phil S Baran
Journal:  J Am Chem Soc       Date:  2014-03-21       Impact factor: 15.419

6.  One-pot, three-component arylalkynyl sulfone synthesis.

Authors:  C Chun Chen; Jerome Waser
Journal:  Org Lett       Date:  2015-01-29       Impact factor: 6.005

7.  Combining organometallic reagents, the sulfur dioxide surrogate DABSO, and amines: a one-pot preparation of sulfonamides, amenable to array synthesis.

Authors:  Alex S Deeming; Claire J Russell; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

8.  Copper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling.

Authors:  Yiding Chen; Michael C Willis
Journal:  Chem Sci       Date:  2017-02-28       Impact factor: 9.825

9.  DABSO-based, three-component, one-pot sulfone synthesis.

Authors:  Alex S Deeming; Claire J Russell; Alan J Hennessy; Michael C Willis
Journal:  Org Lett       Date:  2013-12-05       Impact factor: 6.005

10.  Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation.

Authors:  Alex S Deeming; Claire J Russell; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-24       Impact factor: 15.336
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