Literature DB >> 18720992

Carbonylation of aryl chlorides with oxygen nucleophiles at atmospheric pressure. Preparation of phenyl esters as acyl transfer agents and the direct preparation of alkyl esters and carboxylic acids.

Donald A Watson1, Xuexiang Fan, Stephen L Buchwald.   

Abstract

A mild, functional group tolerant method of the preparation of phenyl esters from aryl chlorides via palladium-catalyzed carbonylation is described using atmospheric pressure of carbon monoxide. Phenyl esters are shown to be useful acylating agents, delivering libraries of carbonyl derivatives, including alkyl, allyl and thioesters, under very mild conditions. Direct preparation of alkyl esters and carboxylic acids is also demonstrated, providing the first method for the preparation of methyl and ethyl esters from aryl chlorides without pressured reactors.

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Year:  2008        PMID: 18720992     DOI: 10.1021/jo800907e

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  11 in total

1.  Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst.

Authors:  Jianxia Chen; E Namila; Chaolumen Bai; Menghe Baiyin; Bao Agula; Yong-Sheng Bao
Journal:  RSC Adv       Date:  2018-07-13       Impact factor: 4.036

2.  Radical differentiation of two ester groups in unsymmetrical diazomalonates for highly asymmetric olefin cyclopropanation.

Authors:  Jingyi Wang; Jingjing Xie; Wan-Chen Cindy Lee; Duo-Sheng Wang; X Peter Zhang
Journal:  Chem Catal       Date:  2021-12-29

3.  Potent inhibition of alcohol self-administration in alcohol-preferring rats by a κ-opioid receptor antagonist.

Authors:  John R Cashman; Marc R Azar
Journal:  J Pharmacol Exp Ther       Date:  2014-05-09       Impact factor: 4.030

4.  Highly enantioselective three-component direct Mannich reactions of unfunctionalized ketones catalyzed by bifunctional organocatalysts.

Authors:  Qunsheng Guo; John Cong-Gui Zhao
Journal:  Org Lett       Date:  2013-01-23       Impact factor: 6.005

Review 5.  Heterogeneous Phase Microwave-Assisted Reactions under CO₂ or CO Pressure.

Authors:  Emanuela Calcio Gaudino; Laura Rinaldi; Laura Rotolo; Diego Carnaroglio; Camillo Pirola; Giancarlo Cravotto
Journal:  Molecules       Date:  2016-02-24       Impact factor: 4.411

6.  Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes.

Authors:  Zhenbo Yuan; Yuye Zeng; Ziwen Feng; Zhe Guan; Aijun Lin; Hequan Yao
Journal:  Nat Commun       Date:  2020-05-21       Impact factor: 14.919

7.  Formal Synthesis of (±)-Allocolchicine Via Gold-Catalysed Direct Arylation: Implication of Aryl Iodine(III) Oxidant in Catalyst Deactivation Pathways.

Authors:  Tom J A Corrie; Guy C Lloyd-Jones
Journal:  Top Catal       Date:  2017-04-19       Impact factor: 2.910

8.  Metal- and Solvent-Free Transesterification and Aldol Condensation Reactions by a Homogenous Recyclable Basic Ionic Liquid Based on the 1,3,5-Triazine Framework.

Authors:  Yanqiu Hu; Mingqi Ren; Milad Kazemnejadi
Journal:  ChemistryOpen       Date:  2021-08       Impact factor: 2.630

9.  A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts.

Authors:  Jeffrey S Quesnel; Alexander Fabrikant; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2015-09-30       Impact factor: 9.825

10.  Ester dance reaction on the aromatic ring.

Authors:  Kaoru Matsushita; Ryosuke Takise; Kei Muto; Junichiro Yamaguchi
Journal:  Sci Adv       Date:  2020-07-08       Impact factor: 14.136

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