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Synlett 2012(3): 463-467  
DOI: 10.1055/s-0031-1290320
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Regioselective Arylation of Arene C-H Bond Assisted by the Removable 2-Pyridylsulfinyl Group

Xunbin Zhanga, Ming Yua, Jinzhong Yaoa, Yuhong Zhang*a,b
a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87953244; e-Mail: yhzhang@zju.edu.cn;
b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
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Publication History

Received 26 October 2011
Publication Date:
25 January 2012 (online)

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Abstract

A palladium-catalyzed arylation of arene C-H bond assisted by a removable 2-pyridylsulfinyl group is described. The reaction employs aryltrifluoroborates as the arylation reagent, leading to the corresponding products in moderate to good yield with broad substrate scope. The directing group can be removed or converted to other useful functionalities, which showcases the potential synthetic application of the methodology.

Key words

C-H bond activation - arylation - aryltrifluoroborate - sulfoxide - palladium catalysis

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