Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C–H Bond Cleavage

Mochida, Satoshi; Umeda, Nobuyoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro

doi:10.1246/cl.2010.744

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Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C–H Bond Cleavage

Author(s): Satoshi Mochida , Nobuyoshi Umeda , Koji Hirano , Tetsuya Satoh , Masahiro Miura

Publication date Created: July 05 2010

Publication date (Print): July 05 2010

Journal: Chemistry Letters

Publisher: The Chemical Society of Japan

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Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Xiao Chen, Keary M Engle, Dong-Hui Wang … (2009)

In the past decade, palladium-catalyzed C-H activation/C-C bond-forming reactions have emerged as promising new catalytic transformations; however, development in this field is still at an early stage compared to the state of the art in cross-coupling reactions using aryl and alkyl halides. This Review begins with a brief introduction of four extensively investigated modes of catalysis for forming C-C bonds from C-H bonds: Pd(II)/Pd(0), Pd(II)/Pd(IV), Pd(0)/Pd(II)/Pd(IV), and Pd(0)/Pd(II) catalysis. A more detailed discussion is then directed towards the recent development of palladium(II)-catalyzed coupling of C-H bonds with organometallic reagents through a Pd(II)/Pd(0) catalytic cycle. Despite the progress made to date, improving the versatility and practicality of this new reaction remains a tremendous challenge.