Thioether-directed acetoxylation of C(sp2)–H bonds of arenes by palladium catalysis

Binjie Wang; Cong Lin; Yue Liu; Zili Fan; Zhanxiang Liu; Yuhong Zhang

doi:10.1039/C5QO00144G

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Thioether-directed acetoxylation of C(sp²)–H bonds of arenes by palladium catalysis†

Binjie Wang,^a Cong Lin,^a Yue Liu,^a Zili Fan,^a Zhanxiang Liu*^a and Yuhong Zhang*^ab

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* Corresponding authors

^a ZJU-NHU United R&D Center, Department of Chemistry, Zhejiang University, Hangzhou 310027, China
E-mail: liuzhanx@zju.edu.cn, yhzhang@zju.edu.cn

^b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Abstract

The palladium-catalyzed acetoxylation of aromatic C(sp²)–H bonds utilizing thioether as the directing group was developed. Both benzyl sulfides and phenethyl sulfides could react with PhI(OAc)₂ to afford the site-selectively acetoxylated products in good yields. The directing groups could be further transformed into synthetically useful functional groups or successfully removed.

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Article information

DOI: https://doi.org/10.1039/C5QO00144G
Article type: Research Article
Submitted: 29 Apr 2015
Accepted: 11 Jun 2015
First published: 12 Jun 2015

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Org. Chem. Front., 2015,2, 973-977

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Thioether-directed acetoxylation of C(sp²)–H bonds of arenes by palladium catalysis

B. Wang, C. Lin, Y. Liu, Z. Fan, Z. Liu and Y. Zhang, Org. Chem. Front., 2015, 2, 973 DOI: 10.1039/C5QO00144G

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