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

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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

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Corresponding authors

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

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

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

DOI: 10.1039/C2CC37352A
Received 08 Oct 2012, Accepted 03 Dec 2012
First published online 03 Dec 2012

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Abstract
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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.