C(sp3)–H activation-enabled cross-coupling of two aryl halides: an approach to 9,10-dihydrophenanthrenes

Yichao Gu; Xueliang Sun; Bin Wan; Zhuoer Lu; Yanghui Zhang

doi:10.1039/D0CC04602G

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C(sp³)–H activation-enabled cross-coupling of two aryl halides: an approach to 9,10-dihydrophenanthrenes†

Yichao Gu,^a Xueliang Sun,^a Bin Wan,^a Zhuoer Lu^a and Yanghui Zhang

*^a

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* Corresponding authors

^a School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China
E-mail: zhangyanghui@tongji.edu.cn

Abstract

A palladium-catalyzed cross-coupling reaction of aryl halides with 2-chlorobenzoic acids has been developed. The reaction forms C(sp³), C(sp²)-palladacycles through C(sp³)–H activation. The palladacycles react with 2-chlorobenzoic acids through two successive C–C cross-couplings, and two C–C bonds are formed with high chemoselectivity. The reaction provides an innovative method for the synthesis of 9,10-dihydrophenanthrenes.

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Article information

DOI: https://doi.org/10.1039/D0CC04602G
Article type: Communication
Submitted: 03 Jul 2020
Accepted: 05 Aug 2020
First published: 06 Aug 2020

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Chem. Commun., 2020,56, 10942-10945

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C(sp³)–H activation-enabled cross-coupling of two aryl halides: an approach to 9,10-dihydrophenanthrenes

Y. Gu, X. Sun, B. Wan, Z. Lu and Y. Zhang, Chem. Commun., 2020, 56, 10942 DOI: 10.1039/D0CC04602G

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