Literature DB >> 21510692

Mild Pd-catalyzed N-arylation of methanesulfonamide and related nucleophiles: avoiding potentially genotoxic reagents and byproducts.

Brandon R Rosen1, J Craig Ruble, Thomas J Beauchamp, Antonio Navarro.   

Abstract

A convenient, general, and high yielding Pd-catalyzed cross-coupling of methanesulfonamide with aryl bromides and chlorides is reported. The use of this method eliminates concern over genotoxic impurities that can arise when an aniline is reacted with methanesulfonyl chloride. The application of this method to the synthesis of dofetilide is also reported.

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Year:  2011        PMID： 21510692     DOI： 10.1021/ol200660s

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


  10 in total

1.  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

2.  Sulfonamides Are an Overlooked Class of Electron Donors in Luminogenic Luciferins and Fluorescent Dyes.

Authors:  Deepak K Sharma; Spencer T Adams; Kate L Liebmann; Adam Choi; Stephen C Miller
Journal:  Org Lett       Date:  2019-03-05       Impact factor: 6.005

3.  Efficient palladium-catalyzed cross-coupling of highly acidic substrates, nitroacetates.

Authors:  Alison E Metz; Simon Berritt; Spencer D Dreher; Marisa C Kozlowski
Journal:  Org Lett       Date:  2012-01-20       Impact factor: 6.005

4.  Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters.

Authors:  J Miles Blackburn; Anastasia L Gant Kanegusuku; Georgia E Scott; Jennifer L Roizen
Journal:  Org Lett       Date:  2019-08-22       Impact factor: 6.005

5.  Iodine-catalyzed sulfonylation of sulfonyl hydrazides with tert-amines: a green and efficient protocol for the synthesis of sulfonamides.

Authors:  Jinyang Chen; Xiaoran Han; Lan Mei; Jinchuan Liu; Kui Du; Tuanwu Cao; Qiang Li
Journal:  RSC Adv       Date:  2019-10-02       Impact factor: 4.036

6.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

Review 7.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

8.  Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

Authors:  Nicholas C Bruno; Matthew T Tudge; Stephen L Buchwald
Journal:  Chem Sci       Date:  2013       Impact factor: 9.825

9.  A tunable pair electrochemical strategy for the synthesis of new benzenesulfonamide derivatives.

Authors:  Banafsheh Mokhtari; Davood Nematollahi; Hamid Salehzadeh
Journal:  Sci Rep       Date:  2019-03-14       Impact factor: 4.379

10.  Base-Mediated Coupling Reactions of Benzenesulfonyl Azides with Proline: Synthesis of Proline-Derived Benzenesulfonamides.

Authors:  Hongyan Liu; Bin Zhang; Wei Zhao; Xiao Yu; Wenjing Zhu; Chengcai Xia; Yanmeng Zhou
Journal:  ACS Omega       Date:  2021-12-07
  10 in total

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