Literature DB >> 20180566

A highly efficient palladium/copper cocatalytic system for direct arylation of heteroarenes: an unexpected effect of Cu(Xantphos)I.

Jinkun Huang1, Johann Chan, Ying Chen, Christopher J Borths, Kyle D Baucom, Robert D Larsen, Margaret M Faul.   

Abstract

Heteroarenes are important structural moieties in many chemical industry fields. A highly efficient Pd/Cu-catalyzed C-H arylation method for a range of heterocycles has been discovered. It was found that the key to the success of this transformation is a combination of a palladium catalyst and a well-defined copper cocatalyst. The efficiency and low loadings of catalyst (0.25 mol %) and cocatalyst (1 mol %) together with the mild reaction conditions demonstrate this method to be practically useful and mechanistically interesting.

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Year:  2010        PMID： 20180566     DOI： 10.1021/ja100354j

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


  12 in total

1.  Mechanistic studies on direct arylation of pyridine N-oxide: evidence for cooperative catalysis between two distinct palladium centers.

Authors:  Yichen Tan; Fabiola Barrios-Landeros; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-02-17       Impact factor: 15.419

2.  A general method for copper-catalyzed arene cross-dimerization.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-08-08       Impact factor: 15.419

3.  Enantioselective Preparation of Arenes with β-Stereogenic Centers: Confronting the 1,1-Disubstituted Olefin Problem Using CuH/Pd Cooperative Catalysis.

Authors:  Zhaohong Lu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-30       Impact factor: 15.336

4.  A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors:  Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

5.  Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

Authors:  Feng Gao; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chem Commun (Camb)       Date:  2014-07-31       Impact factor: 6.222

6.  Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling.

Authors:  Chengwei Liu; Chong-Lei Ji; Tongliang Zhou; Xin Hong; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2021-04-06       Impact factor: 15.336

7.  Pd(II)-catalyzed ortho arylation of 2-arylbenzothiazoles with aryl iodides via benzothiazole-directed C-H activation.

Authors:  Qiuping Ding; Huafang Ji; Dan Wang; Yuqing Lin; Weihua Yu; Yiyuan Peng
Journal:  J Organomet Chem       Date:  2012-07-15       Impact factor: 2.369

8.  Copper-catalyzed Direct 2-Arylation of Benzoxazoles and Benzoimidazoles with Aryl Bromides and Cytotoxicity of Products.

Authors:  Nan-Nan Jia; Xin-Chuan Tian; Xiao-Xia Qu; Xing-Xiu Chen; Ya-Nan Cao; Yun-Xin Yao; Feng Gao; Xian-Li Zhou
Journal:  Sci Rep       Date:  2017-03-03       Impact factor: 4.379

9.  Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis.

Authors:  Stig D Friis; Michael T Pirnot; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

10.  Gold-catalyzed tandem reactions of amide-aldehyde-alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles.

Authors:  Pierre Querard; Simon A Girard; Nick Uhlig; Chao-Jun Li
Journal:  Chem Sci       Date:  2015-10-06       Impact factor: 9.825
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