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铑催化香豆素的Csp-H芳基化反应的无痕活化策略

Traceless-Activation Strategy for Rh-Catalyzed Csp-H Arylation of Coumarins.

作者信息

Han Fuzhong, Xun Shanshan, Jia Lina, Zhang Yutong, Zou Liwei, Hu Xiangping

机构信息

College of Chemistry and Chemical Engineering , Qiqihar University , Qiqihar 161006 , China.

Dalian Institute of Chemical Physics , Chinese Academy of Sciences , 457 Zhongshan Road , Dalian 116023 , China.

出版信息

Org Lett. 2019 Aug 2;21(15):5907-5911. doi: 10.1021/acs.orglett.9b02040. Epub 2019 Jul 12.

Abstract

A traceless-activation strategy for the synthesis of 4-arylchroman-2-ones via a Rh(III)-catalyzed C-H activation of 2-arylpyridines and subsequent conjugated/decarboxylative addition to coumarin-3-carboxylic acids has been reported. The carboxyl group at C3 position of coumarin proved to be crucial to realize the reaction, which is spontaneously removed after the reaction by the release of CO. The reaction displayed good substrate tolerance and gave various 4-arylchroman-2-ones in up to 90% yield.

摘要

据报道,通过铑(III)催化的2-芳基吡啶的C-H活化以及随后与香豆素-3-羧酸的共轭/脱羧加成反应,开发了一种无痕活化策略用于合成4-芳基色满-2-酮。结果表明,香豆素C3位的羧基对于实现该反应至关重要,反应后通过释放CO2自发地脱除该羧基。该反应表现出良好的底物耐受性,能以高达90%的产率得到各种4-芳基色满-2-酮。

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