Literature DB >> 24256546

Palladium-catalyzed sulfination of aryl and heteroaryl halides: direct access to sulfones and sulfonamides.

Andrei Shavnya1, Steven B Coffey, Aaron C Smith, Vincent Mascitti.   

Abstract

A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.

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Year:  2013        PMID: 24256546     DOI: 10.1021/ol403072r

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


  19 in total

1.  Application of fundamental organometallic chemistry to the development of a gold-catalyzed synthesis of sulfinate derivatives.

Authors:  Miles W Johnson; Scott W Bagley; Neal P Mankad; Robert G Bergman; Vincent Mascitti; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-20       Impact factor: 15.336

2.  Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent.

Authors:  Hang T Dang; Vu T Nguyen; Viet D Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  Org Biomol Chem       Date:  2018-05-15       Impact factor: 3.876

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

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Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

4.  Amine-Catalyzed Copper-Mediated C-H Sulfonylation of Benzaldehydes via a Transient Imine Directing Group.

Authors:  Joe I Higham; James A Bull
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-05       Impact factor: 16.823

5.  Catalytic diastereo- and enantioselective additions of versatile allyl groups to N-H ketimines.

Authors:  Hwanjong Jang; Filippo Romiti; Sebastian Torker; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-07-17       Impact factor: 24.427

6.  Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions.

Authors:  Jacob J Day; Deshka L Neill; Shi Xu; Ming Xian
Journal:  Org Lett       Date:  2017-07-03       Impact factor: 6.005

7.  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

8.  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

9.  Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides.

Authors:  Tim Markovic; Benjamin N Rocke; David C Blakemore; Vincent Mascitti; Michael C Willis
Journal:  Chem Sci       Date:  2017-04-28       Impact factor: 9.825

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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