Synlett 2012; 23(18): 2714-2718
DOI: 10.1055/s-0032-1317350
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© Georg Thieme Verlag Stuttgart · New York

Direct Oxidative C–H Arylation of Benzoxazoles with Arylsulfonyl Hydrazides Promoted by Palladium Complexes

On Ying Yuen
State Key Laboratory of Chirosciences, PolyU Shenzhen Research Institute (SZRI) and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China   Fax: +852(2364)9932   Email: fuk-yee.kwong@polyu.edu.hk
,
Chau Ming So
State Key Laboratory of Chirosciences, PolyU Shenzhen Research Institute (SZRI) and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China   Fax: +852(2364)9932   Email: fuk-yee.kwong@polyu.edu.hk
,
Wing Tak Wong
State Key Laboratory of Chirosciences, PolyU Shenzhen Research Institute (SZRI) and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China   Fax: +852(2364)9932   Email: fuk-yee.kwong@polyu.edu.hk
,
Fuk Yee Kwong*
State Key Laboratory of Chirosciences, PolyU Shenzhen Research Institute (SZRI) and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China   Fax: +852(2364)9932   Email: fuk-yee.kwong@polyu.edu.hk
› Author Affiliations
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Publication History

Received: 21 August 2012

Accepted after revision: 11 September 2012

Publication Date:
09 October 2012 (online)


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Abstract

This study describes a direct oxidative C-2 arylation of benzoxazoles using arylsulfonyl hydrazides as the aryl sources. A simple catalyst system [Pd(OAc)2 and Ph3P] allows the reactions to proceed smoothly under oxidative reaction conditions. Other ­heteroarenes such as caffeine and benzothiazole are also applicable substrates. Notably, this catalytic system tolerates halogen substituents which provides a useful complement to the current cross-­coupling reactions which use aryl halides.

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