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钯催化芳基酰基过氧化物对C-H键的脱羧芳基化反应。

Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides.

作者信息

Yu Wing-Yiu, Sit Wing Nga, Zhou Zhongyuan, Chan Albert S-C

机构信息

Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis and the Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.

出版信息

Org Lett. 2009 Aug 6;11(15):3174-7. doi: 10.1021/ol900756g.

DOI:10.1021/ol900756g
PMID:19583200
Abstract

A Pd(OAc)(2)-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.

摘要

开发了一种醋酸钯(II)催化的芳族C-H键脱羧芳基化反应方法,该方法使用芳基过氧酰作为廉价的芳基源。含有吡啶基、肟基和恶唑啉基的底物能有效地进行邻位选择性C-H芳基化反应,且具有出色的官能团耐受性。该芳基化反应应首先通过导向基团辅助的环钯化反应开始,随后钯环与过氧化物热分解原位生成的芳基自由基发生反应。

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