Literature DB >> 23837740

Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids.

J Robb DeBergh1, Nootaree Niljianskul, Stephen L Buchwald.   

Abstract

A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.

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Year:  2013        PMID： 23837740      PMCID： PMC3766840          DOI： 10.1021/ja405949a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  24 in total

1.  Preparation of arylsulfonyl chlorides by chlorosulfonylation of in situ generated diazonium salts using a continuous flow reactor.

Authors:  Laia Malet-Sanz; Julia Madrzak; Steven V Ley; Ian R Baxendale
Journal:  Org Biomol Chem       Date:  2010-09-27       Impact factor: 3.876

2.  A convenient preparation of heteroaryl sulfonamides and sulfonyl fluorides from heteroaryl thiols.

Authors:  Stephen W Wright; Kelly N Hallstrom
Journal:  J Org Chem       Date:  2006-02-03       Impact factor: 4.354

3.  Synthesis of functional aromatic multisulfonyl chlorides and their masked precursors.

Authors:  V Percec; T K Bera; B B De; Y Sanai; J Smith; M N Holerca; B Barboiu; R B Grubbs; J M Fréchet
Journal:  J Org Chem       Date:  2001-03-23       Impact factor: 4.354

4.  A palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines.

Authors:  Shengqing Ye; Jie Wu
Journal:  Chem Commun (Camb)       Date:  2012-06-29       Impact factor: 6.222

5.  The role of reversible oxidative addition in selective palladium(0)-catalyzed intramolecular cross-couplings of polyhalogenated substrates: synthesis of brominated indoles.

Authors:  Stephen G Newman; Mark Lautens
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

6.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Trichlorophenol (TCP) sulfonate esters: a selective alternative to pentafluorophenol (PFP) esters and sulfonyl chlorides for the preparation of sulfonamides.

Authors:  Jonathan D Wilden; Lynsey Geldeard; Chieh C Lee; Duncan B Judd; Stephen Caddick
Journal:  Chem Commun (Camb)       Date:  2006-12-21       Impact factor: 6.222

8.  Observations on the reactivity of pentafluorophenyl sulfonate esters.

Authors:  Stephen Caddick; Jonathan D Wilden; Duncan B Judd
Journal:  Chem Commun (Camb)       Date:  2005-04-15       Impact factor: 6.222

9.  Palladium-catalyzed aminosulfonylation of aryl halides.

Authors:  Bao Nguyen; Edward J Emmett; Michael C Willis
Journal:  J Am Chem Soc       Date:  2010-10-28       Impact factor: 15.419

10.  Direct conversion of thiols to sulfonyl chlorides and sulfonamides.

Authors:  Kiumars Bahrami; Mohammad M Khodaei; Mehdi Soheilizad
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354
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  16 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.  Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.

Authors:  Bing Zheng; Minyan Li; Gui Gao; Yuying He; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2016-06-15       Impact factor: 5.837

3.  Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines.

Authors:  Nathaniel H Park; Ekaterina V Vinogradova; David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

4.  Ligand Promoted meta-C-H Chlorination of Anilines and Phenols.

Authors:  Hang Shi; Peng Wang; Shin Suzuki; Marcus E Farmer; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-11-08       Impact factor: 15.419

5.  Synthesis of diverse pyrazole-4-sulfonyl chlorides starting from 2-(benzylthio)malonaldehyde.

Authors:  Pavlo A Sokolyuk; Ivan S Kondratov; Olexiy V Gavrylenko; Andrey A Tolmachov
Journal:  Mol Divers       Date:  2015-09-12       Impact factor: 2.943

Review 6.  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

Review 7.  Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

Authors:  Renhe Li; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2020-10-05       Impact factor: 15.419

8.  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

9.  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

10.  Modular Synthesis of Alkenyl Sulfamates and β-Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement.

Authors:  Felipe Cesar Sousa E Silva; Katarzyna Doktor; Quentin Michaudel
Journal:  Org Lett       Date:  2021-06-20       Impact factor: 6.072
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