Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides

Yinuo Wu; Pui Ying Choy; Fei Mao; Fuk Yee Kwong

doi:10.1039/C2CC37352A

Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides

Yinuo Wu,^a Pui Ying Choy,^a Fei Mao^b and Fuk Yee Kwong*^a

* Corresponding authors

^a State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong
E-mail: fuk-yee.kwong@polyu.edu.hk
Fax: +852-2364-9932

^b School of Pharmaceutical Sciences, Sun Yat-sen University, China

Abstract

A palladium-catalyzed cascade cross-coupling of acetanilide and toluene for the synthesis of ortho-acylacetanilide is described. Toluene derivatives can act as effective acyl precursors (upon sp³-C–H bond oxidation by a Pd/TBHP system) in the oxidative coupling between two C–H bonds. This dehydrogenative Pd-catalyzed ortho-acylation proceeds under mild reaction conditions.

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Publication details

The article was received on 08 Oct 2012, accepted on 03 Dec 2012 and first published on 03 Dec 2012

Article type: Communication

DOI: 10.1039/C2CC37352A

Citation: Chem. Commun., 2013,49, 689-691

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Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides

Y. Wu, P. Y. Choy, F. Mao and F. Y. Kwong, Chem. Commun., 2013, 49, 689
DOI: 10.1039/C2CC37352A
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Chemical Communications

Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides

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Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides

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