Literature DB >> 22870867

Decarbonylative C-H coupling of azoles and aryl esters: unprecedented nickel catalysis and application to the synthesis of muscoride A.

Kazuma Amaike1, Kei Muto, Junichiro Yamaguchi, Kenichiro Itami.   

Abstract

A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.

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Year:  2012        PMID: 22870867     DOI: 10.1021/ja306062c

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


  37 in total

1.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

2.  Alkyl-(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis.

Authors:  Frederik Sandfort; Matthew J O'Neill; Josep Cornella; Laurin Wimmer; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-10       Impact factor: 15.336

3.  Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates.

Authors:  Jennifer M Crawford; Kyle E Shelton; Emily K Reeves; Bryce K Sadarananda; Dipannita Kalyani
Journal:  Org Chem Front       Date:  2015-05-12       Impact factor: 5.281

4.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

5.  Well-defined nickel and palladium precatalysts for cross-coupling.

Authors:  Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal:  Nat Rev Chem       Date:  2017-03-01       Impact factor: 34.035

6.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

7.  Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers.

Authors:  Naoko Ichiishi; Christian A Malapit; Łukasz Woźniak; Melanie S Sanford
Journal:  Org Lett       Date:  2017-12-07       Impact factor: 6.005

8.  Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides.

Authors:  Christian A Malapit; Naoko Ichiishi; Melanie S Sanford
Journal:  Org Lett       Date:  2017-07-19       Impact factor: 6.005

9.  Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oximes.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2012-12-07       Impact factor: 6.222

10.  Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters.

Authors:  Liana Hie; Noah F Fine Nathel; Xin Hong; Yun-Fang Yang; Kendall N Houk; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-25       Impact factor: 15.336

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