Literature DB >> 21192682

Rhodium(I)-catalyzed direct carboxylation of arenes with CO2 via chelation-assisted C-H bond activation.

Hajime Mizuno1, Jun Takaya, Nobuharu Iwasawa.   

Abstract

Rh-catalyzed direct carboxylation of unactivated aryl C-H bond under atmospheric pressure of carbon dioxide was realized via chelation-assisted C-H activation for the first time. Variously substituted and functionalized 2-arylpyridines and 1-arylpyrazoles underwent the carboxylation in the presence of the rhodium catalyst and a stoichiometric methylating reagent, AlMe(2)(OMe), to give carboxylated products in good yields. The catalysis is proposed to consist of methylrhodium(I) species as the key intermediate, which undergoes C-H activation to afford rhodium(III), followed by reductive elimination of methane to give nucleophilic arylrhodium(I). This approach demonstrates promising application of C-H bond activation strategy in the field of carbon dioxide fixation.

Entities:  

Year:  2010        PMID: 21192682     DOI: 10.1021/ja109097z

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


  11 in total

Review 1.  Silver and gold-catalyzed multicomponent reactions.

Authors:  Giorgio Abbiati; Elisabetta Rossi
Journal:  Beilstein J Org Chem       Date:  2014-02-26       Impact factor: 2.883

Review 2.  Metal-Catalyzed Carboxylation of Organic (Pseudo)halides with CO2.

Authors:  Marino Börjesson; Toni Moragas; Daniel Gallego; Ruben Martin
Journal:  ACS Catal       Date:  2016-08-30       Impact factor: 13.084

3.  Mechanistic study of the rhodium-catalyzed carboxylation of simple aromatic compounds with carbon dioxide.

Authors:  Takuya Suga; Takanobu Saitou; Jun Takaya; Nobuharu Iwasawa
Journal:  Chem Sci       Date:  2016-11-01       Impact factor: 9.825

4.  Carbon Dioxide Utilization by the Five-Membered Ring Products of Cyclometalation Reactions.

Authors:  Iwao Omae
Journal:  Curr Org Chem       Date:  2016-04       Impact factor: 2.180

5.  Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2.

Authors:  Si-Shun Yan; Lei Zhu; Jian-Heng Ye; Zhen Zhang; He Huang; Huiying Zeng; Chao-Jun Li; Yu Lan; Da-Gang Yu
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

6.  Formal C-H Carboxylation of Unactivated Arenes.

Authors:  Ashot Gevorgyan; Kathrin H Hopmann; Annette Bayer
Journal:  Chemistry       Date:  2020-05-04       Impact factor: 5.236

7.  Photocarboxylation of Benzylic C-H Bonds.

Authors:  Qing-Yuan Meng; Tobias E Schirmer; Anna Lucia Berger; Karsten Donabauer; Burkhard König
Journal:  J Am Chem Soc       Date:  2019-07-11       Impact factor: 15.419

8.  Site-Selective, Remote sp3 C-H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis.

Authors:  Basudev Sahoo; Peter Bellotti; Francisco Juliá-Hernández; Qing-Yuan Meng; Stefano Crespi; Burkhard König; Ruben Martin
Journal:  Chemistry       Date:  2019-06-06       Impact factor: 5.236

Review 9.  C-H Carboxylation of Aromatic Compounds through CO2 Fixation.

Authors:  Junfei Luo; Igor Larrosa
Journal:  ChemSusChem       Date:  2017-08-16       Impact factor: 8.928

Review 10.  Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source.

Authors:  Tetsuaki Fujihara; Yasushi Tsuji
Journal:  Beilstein J Org Chem       Date:  2018-09-19       Impact factor: 2.883

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