Literature DB >> 24288654

Copper-Catalyzed Carboxylation of Aryl Iodides with Carbon Dioxide.

Hung Tran-Vu1, Olafs Daugulis.   

Abstract

A method for carboxylation of aryl iodides with carbon dioxide has been developed. The reaction employs low loadings of copper iodide/TMEDA or DMEDA catalyst, 1 atm of CO2, DMSO or DMA solvent, and proceeds at 25-70 °C. Good functional group tolerance is observed, with ester, bromide, chloride, fluoride, ether, hydroxy, amino, and ketone functionalities tolerated. Additionally, hindered aryl iodides such as iodomesitylene can also be carboxylated.

Entities:  

Keywords:  Carbon dioxide; arenecarboxylic acids; aryl halides; carboxylation; copper catalysis

Year:  2013        PMID: 24288654      PMCID: PMC3839347          DOI: 10.1021/cs400443p

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  25 in total

1.  Nucleophilic catalysis of the iodine-zinc exchange reaction: preparation of highly functionalized diaryl zinc compounds.

Authors:  Florian F Kneisel; Maximilian Dochnahl; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-13       Impact factor: 15.336

2.  Direct C-H carboxylation with complexes of the coinage metals.

Authors:  Ine I F Boogaerts; Steven P Nolan
Journal:  Chem Commun (Camb)       Date:  2010-12-17       Impact factor: 6.222

3.  Transformation of carbon dioxide.

Authors:  Toshiyasu Sakakura; Jun-Chul Choi; Hiroyuki Yasuda
Journal:  Chem Rev       Date:  2007-06       Impact factor: 60.622

4.  Preparation of organometallic compounds from highly reactive metal powders.

Authors:  R D Rieke
Journal:  Science       Date:  1989-12-08       Impact factor: 47.728

5.  Metal-catalyzed carboxylation of organometallic reagents with carbon dioxide.

Authors:  Arkaitz Correa; Rubén Martín
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Transition-metal-catalyzed carboxylation of C-H bonds.

Authors:  Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-22       Impact factor: 15.336

7.  Nickel-catalyzed reductive carboxylation of styrenes using CO2.

Authors:  Catherine M Williams; Jeffrey B Johnson; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2008-10-17       Impact factor: 15.419

8.  Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids.

Authors:  Paul R Blakemore; Stephen P Marsden; Huw D Vater
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

9.  Ni-catalyzed direct carboxylation of benzyl halides with CO2.

Authors:  Thierry León; Arkaitz Correa; Ruben Martin
Journal:  J Am Chem Soc       Date:  2013-01-14       Impact factor: 15.419

10.  Carbon dioxide as a carbon source in organic transformation: carbon-carbon bond forming reactions by transition-metal catalysts.

Authors:  Yasushi Tsuji; Tetsuaki Fujihara
Journal:  Chem Commun (Camb)       Date:  2012-10-14       Impact factor: 6.222

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  5 in total

1.  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

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.  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 4.  Advances in Palladium-Catalyzed Carboxylation Reactions.

Authors:  Lucia Veltri; Roberta Amuso; Raffaella Mancuso; Bartolo Gabriele
Journal:  Molecules       Date:  2022-01-01       Impact factor: 4.411

Review 5.  New trends and applications in carboxylation for isotope chemistry.

Authors:  Ryan A Bragg; Malvika Sardana; Markus Artelsmair; Charles S Elmore
Journal:  J Labelled Comp Radiopharm       Date:  2018-05-30       Impact factor: 1.921

  5 in total

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