Literature DB >> 24038854

Cascade palladium catalysis: a predictable and selectable regiocontrolled synthesis of N-arylbenzimidazoles.

Nathan T Jui1, Stephen L Buchwald.   

Abstract

By choice: The palladium-catalyzed cascade reaction of 2-chloroaryl sulfonates with arylamine and amide nucleophiles provides direct access to N-arylbenzimidazoles. This strategy selectively produces the heterocycles based on chemoselective oxidative addition. 2-Chloroaryl triflates (Tf) produce one regioisomer and the corresponding 2-chloroaryl mesylates (Ms) deliver the other in a selectable manner.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  chemoselectivity; cross-coupling; heterocycles; palladium; synthetic methods

Mesh：

Substances：

Year:  2013        PMID： 24038854      PMCID： PMC3875363          DOI： 10.1002/anie.201306007

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  36 in total

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Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

2.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

Review 3.  Developments towards regioselective synthesis of 1,2-disubstituted benzimidazoles.

Authors:  Luísa C R Carvalho; Eduarda Fernandes; M Manuel B Marques
Journal:  Chemistry       Date:  2011-10-11       Impact factor: 5.236

4.  Copper-catalyzed intramolecular C-N bond formation: a straightforward synthesis of benzimidazole derivatives in water.

Authors:  Jinsong Peng; Min Ye; Cuijuan Zong; Fangyun Hu; Lingtong Feng; Xiaoyan Wang; Yufeng Wang; Chunxia Chen
Journal:  J Org Chem       Date:  2010-12-22       Impact factor: 4.354

5.  A protocol to 2-aminobenzimidazoles via copper-catalyzed cascade addition and cyclization of o-haloanilines and carbodiimides.

Authors:  Fei Wang; Shangjun Cai; Qian Liao; Chanjuan Xi
Journal:  J Org Chem       Date:  2011-03-25       Impact factor: 4.354

6.  Copper(I)-catalyzed synthesis of substituted 2-mercapto benzimidazoles.

Authors:  Siva Murru; Bhisma K Patel; Jean Le Bras; Jacques Muzart
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

7.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

8.  Copper-catalyzed synthesis of 2-unsubstituted, N-substituted benzimidazoles.

Authors:  Keiichi Hirano; Akkattu T Biju; Frank Glorius
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

9.  Copper- and palladium-catalyzed intramolecular aryl guanidinylation: an efficient method for the synthesis of 2-aminobenzimidazoles.

Authors:  Ghotas Evindar; Robert A Batey
Journal:  Org Lett       Date:  2003-01-23       Impact factor: 6.005

10.  Copper-catalyzed synthesis of benzimidazoles via cascade reactions of o-haloacetanilide derivatives with amidine hydrochlorides.

Authors:  Daoshan Yang; Hua Fu; Liming Hu; Yuyang Jiang; Yufen Zhao
Journal:  J Org Chem       Date:  2008-08-28       Impact factor: 4.354
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  8 in total

Review 1.  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

2.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457

3.  PIII /PV =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

Authors:  Trevor V Nykaza; Gen Li; Junyu Yang; Michael R Luzung; Alexander T Radosevich
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-29       Impact factor: 15.336

4.  A bioinspired catalytic aerobic oxidative C-H functionalization of primary aliphatic amines: synthesis of 1,2-disubstituted benzimidazoles.

Authors:  Khac Minh Huy Nguyen; Martine Largeron
Journal:  Chemistry       Date:  2015-07-23       Impact factor: 5.236

5.  The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4'-substituted-azobenzenes in different solvents.

Authors:  Po-Yi Chen; Chi-Wei Hsu; Tong-Ing Ho; Jinn-Hsuan Ho
Journal:  RSC Adv       Date:  2021-02-10       Impact factor: 3.361

6.  Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp3)-H amidination.

Authors:  Dianke Xie; Wei He; Jiang Xiao; Yao Wu; Yongjia Guo; Qiang Liu; Cancheng Guo
Journal:  RSC Adv       Date:  2019-03-04       Impact factor: 4.036

7.  Regioselective synthesis of benzimidazolones via cascade C-N coupling of monosubstituted ureas.

Authors:  Johannes B Ernst; Nicholas E S Tay; Nathan T Jui; Stephen L Buchwald
Journal:  Org Lett       Date:  2014-06-27       Impact factor: 6.005

8.  Mild Pd-catalyzed aminocarbonylation of (hetero)aryl bromides with a palladacycle precatalyst.

Authors:  Stig D Friis; Troels Skrydstrup; Stephen L Buchwald
Journal:  Org Lett       Date:  2014-08-04       Impact factor: 6.005
  8 in total

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