Literature DB >> 19886688

Palladium-catalyzed direct carboxylation of aryl bromides with carbon dioxide.

Arkaitz Correa1, Rubén Martín.   

Abstract

A novel protocol for the direct carbon dioxide insertion (CO(2)) into aryl halides in a catalytic manner is presented herein. Unlike other carboxylation methods using CO(2), there is no need for the synthesis of the corresponding organometallic intermediates. Additionally, and in contrast to the well-established carbonylation processes, our protocol does not use highly toxic CO for the preparation of benzoic acids. Furthermore, this method is distinguished by its mild conditions, allowing the tolerance of a wide range of functional groups and substitution patterns. The crucial step of the process involves a challenging catalytic CO(2) insertion into Pd-C bonds.

Entities:  

Year:  2009        PMID: 19886688     DOI: 10.1021/ja905264a

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


  17 in total

1.  Organometallic chemistry: C-H carboxylation takes gold.

Authors:  Derek M Dalton; Tomislav Rovis
Journal:  Nat Chem       Date:  2010-09       Impact factor: 24.427

2.  Development of an Improved System for the Carboxylation of Aryl Halides through Mechanistic Studies.

Authors:  David J Charboneau; Gary W Brudvig; Nilay Hazari; Hannah M C Lant; Andrew K Saydjari
Journal:  ACS Catal       Date:  2019-03-14       Impact factor: 13.084

3.  Milled Dry Ice as a C1 Source for the Carboxylation of Aryl Halides.

Authors:  Connor J O'Brien; David A Nicewicz
Journal:  Synlett       Date:  2021-02-04       Impact factor: 2.170

4.  Copper-Catalyzed Carboxylation of Aryl Iodides with Carbon Dioxide.

Authors:  Hung Tran-Vu; Olafs Daugulis
Journal:  ACS Catal       Date:  2013-10-04       Impact factor: 13.084

5.  Insertion of CO2 Mediated by a (Xantphos)NiI -Alkyl Species.

Authors:  Justin B Diccianni; Chunhua T Hu; Tianning Diao
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-14       Impact factor: 15.336

6.  Regioselective Enzymatic β-Carboxylation of para-Hydroxy- styrene Derivatives Catalyzed by Phenolic Acid Decarboxylases.

Authors:  Christiane Wuensch; Tea Pavkov-Keller; Georg Steinkellner; Johannes Gross; Michael Fuchs; Altijana Hromic; Andrzej Lyskowski; Kerstin Fauland; Karl Gruber; Silvia M Glueck; Kurt Faber
Journal:  Adv Synth Catal       Date:  2015-04-02       Impact factor: 5.837

7.  Stoichiometric Reactions of Acylnickel(II) Complexes with Electrophiles and the Catalytic Synthesis of Ketones.

Authors:  Alexander C Wotal; Ryan D Ribson; Daniel J Weix
Journal:  Organometallics       Date:  2014-07-10       Impact factor: 3.876

Review 8.  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

9.  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

Review 10.  C-H Carboxylation of Aromatic Compounds through CO2 Fixation.

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

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