Palladium-Catalyzed Regioselective C–H Bond Acetoxylation–Alkoxylation of Azoxybenzenes

Meng Sun; Liang Zhang; Cheng-Wen Hua; Zhe Wang; Le-Kai Hou; Su-Xian Cai; Shuang Li

doi:10.1055/s-0035-1560637

Synlett, Table of Contents

Synlett 2015; 26(20): 2843-2848
DOI: 10.1055/s-0035-1560637

letter

Palladium-Catalyzed Regioselective C–H Bond Acetoxylation–Alkoxylation of Azoxybenzenes

Meng Sun*

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

,

Liang Zhang

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

,

Cheng-Wen Hua

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

,

Zhe Wang

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

,

Le-Kai Hou

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

,

Su-Xian Cai

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

,

Shuang Li

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. of China Email: sunmeng@nwu.edu.cn

› Author Affiliations

Abstract

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Abstract

Efficient strategies for the regioselective ortho acetoxylation/alkoxylation of C–H bond of azoxybenzenes in the presence of palladium catalysts were developed using PhI(OAc)₂ as the teminal oxidant. Under the very similar conditions established, both reactions proceeded smoothly and were tolerated by a variety of functional groups.

Key words

palladium-catalyzed - acetoxylation–alkoxylation - C–H bond cleavage - azoxybenzene - regioselective

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18 During the preparation of this manuscript, a similar ortho acetoxylation or alkoxylation of azoxy compounds has been reported. See: Zhang D, Cui X, Yang F, Zhang Q, Zhu Y, Wu Y. Org. Chem. Front. 2015; 2: 951
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