Literature DB >> 19099479

Rhodium-catalyzed direct oxidative carbonylation of aromatic C-H bond with CO and alcohols.

Zheng-Hui Guan1, Zhi-Hui Ren, Stephen M Spinella, Shichao Yu, Yong-Min Liang, Xumu Zhang.   

Abstract

A general protocol for the rhodium-catalyzed oxidative carbonylation of arenes to form esters has been developed. A broad substrate scope has been demonstrated allowing carbonylation of electron-rich, electron-poor, and heterocyclic arenes, and the reaction shows wide functional group tolerance and excellent regioselectivities. Up to 96% yield of ortho-substituted aryl or heteroaryl carboxylic esters were obtained with this methodology. The possible mechanism for the rhodium-catalyzed oxidative carbonylation reaction was proposed in this article. Studies show that Oxone play an important role in the transformation.

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Year:  2009        PMID: 19099479     DOI: 10.1021/ja807167y

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


  7 in total

1.  Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp2 C-H bonds.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2017-05-04       Impact factor: 6.222

2.  General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation.

Authors:  Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-19       Impact factor: 15.336

3.  Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.

Authors:  Eun Jeong Yoo; Masayuki Wasa; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-11-17       Impact factor: 15.419

Review 4.  Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

Authors:  Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

5.  Cobalt-catalyzed direct carbonylation of aminoquinoline benzamides.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Org Lett       Date:  2014-08-22       Impact factor: 6.005

6.  Rh-catalyzed aerobic oxidative cyclization of anilines, alkynes, and CO.

Authors:  Xinyao Li; Jun Pan; Hao Wu; Ning Jiao
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825

7.  Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp3)-H bonds of aliphatic amine substrates.

Authors:  Chao Wang; Li Zhang; Changpeng Chen; Jian Han; Yingming Yao; Yingsheng Zhao
Journal:  Chem Sci       Date:  2015-05-19       Impact factor: 9.825

  7 in total

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