Literature DB >> 28070178

Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.

Bing Zheng1, Minyan Li2, Gui Gao3, Yuying He4, Patrick J Walsh2.   

Abstract

A Palladium-catalyzed α-arylation of sulfonamides with aryl chlorides is presented. A Buchwald type precatalyst formed with Kwong's indole-based ligand enabled this transformation to be compatible with a large variety of methyl sulfonamides and aryl chlorides in good to excellent yields. Importantly, under the optimized reaction conditions, only mono-arylated products were observed. This method has been applied to the efficient synthesis of sumatriptan, which is used to treat migraines.

Entities:  

Keywords:  Palladium-catalyzed; aryl chloride; arylation; sulfonamide; sumatriptan

Year:  2016        PMID： 28070178      PMCID： PMC5218594          DOI： 10.1002/adsc.201600090

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  37 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Palladium-catalyzed direct arylation of heteroarenes with aryl mesylates.

Authors:  Chau Ming So; Chak Po Lau; Fuk Yee Kwong
Journal:  Chemistry       Date:  2010-12-16       Impact factor: 5.236

3.  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

4.  Palladium-catalyzed cross-coupling reactions of aryl mesylates.

Authors:  Chau Ming So; Fuk Yee Kwong
Journal:  Chem Soc Rev       Date:  2011-08-22       Impact factor: 54.564

5.  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

6.  Palladium-catalyzed decarboxylative arylation of potassium cyanoacetate: synthesis of α-diaryl nitriles from aryl halides.

Authors:  Pui Yee Yeung; Kin Ho Chung; Fuk Yee Kwong
Journal:  Org Lett       Date:  2011-05-05       Impact factor: 6.005

7.  A new strategy for the synthesis of benzylic sulfonamides: palladium-catalyzed arylation and sulfonamide metathesis.

Authors:  Jonathan B Grimm; Matthew H Katcher; David J Witter; Alan B Northrup
Journal:  J Org Chem       Date:  2007-09-20       Impact factor: 4.354

8.  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

9.  Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone.

Authors:  Masakazu Nambo; Cathleen M Crudden
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-04       Impact factor: 15.336

10.  Palladium-catalyzed α-arylation of benzylic phosphonates.

Authors:  Sonia Montel; Ludovic Raffier; Yuying He; Patrick J Walsh
Journal:  Org Lett       Date:  2014-02-12       Impact factor: 6.005
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  5 in total

1.  Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr2/NIXANTPHOS-based Catalyst.

Authors:  Gui Gao; Yue Fu; Minyan Li; Bo Wang; Bing Zheng; Shicong Hou; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2017-07-12       Impact factor: 5.837

2.  Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners.

Authors:  Minyan Li; Simon Berritt; Lucas Matuszewski; Guogang Deng; Ana Pascual-Escudero; Grace B Panetti; Michal Poznik; Xiaodong Yang; Jason J Chruma; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2017-10-31       Impact factor: 15.419

3.  Biointeractions of Herbicide Atrazine with Human Serum Albumin: UV-Vis, Fluorescence and Circular Dichroism Approaches.

Authors:  Meiqing Zhu; Lijun Wang; Yu Wang; Jie Zhou; Jie Ding; Wei Li; Yue Xin; Shisuo Fan; Zhen Wang; Yi Wang
Journal:  Int J Environ Res Public Health       Date:  2018-01-11       Impact factor: 3.390

4.  Chemical synthesis, inhibitory activity and molecular mechanism of 1-deoxynojirimycin-chrysin as a potent α-glucosidase inhibitor.

Authors:  Ran Zhang; Yueyue Zhang; Gaiqun Huang; Xiangdong Xin; Liumei Tang; Hao Li; Kwang Sik Lee; Byung Rae Jin; Zhongzheng Gui
Journal:  RSC Adv       Date:  2021-12-01       Impact factor: 4.036

5.  A domino reaction for generating β-aryl aldehydes from alkynes by substrate recognition catalysis.

Authors:  Weiwei Fang; Felix Bauer; Yaxi Dong; Bernhard Breit
Journal:  Nat Commun       Date:  2019-10-25       Impact factor: 14.919
  5 in total

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