Rhodium-Catalyzed Direct Oxidative Carbonylation of Aromatic C−H Bond with CO and Alcohols

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...

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Veröffentlicht in:Journal of the American Chemical Society 2009-01, Vol.131 (2), p.729-733
Hauptverfasser: Guan, Zheng-Hui, Ren, Zhi-Hui, Spinella, Stephen M, Yu, Shichao, Liang, Yong-Min, Zhang, Xumu
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Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja807167y