Transition-Metal-Free C-H Arylation of Unactivated Arenes with 8-Hydroxyquinoline as a Promoter

Xuehua Zheng, Xu-Nian Wu, Jing-Yi Chen, Hai-Bin Luo, Deyan Wu*, Yinuo Wu*

*School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. of China, Email: wyinuo3mail.sysu.edu.cn, wudeyan3mail.sysu.edu.cn

X. Zheng, X.-N. Wu, J.-Y. Chen, H.-B. Luo, D. Wu, Y. Wu, Synthesis, 2018, 50, 1721-1727.

DOI: 10.1055/s-0036-1591874

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Abstract

8-Hydroxyquinoline promotes a transition-metal-free direct C-H arylation of unactivated arenes with aryl bromides to provide biaryl compounds with structural diversity in good yields. Mechanistic studies reveal that the reaction proceeds via a homolytic aromatic substitution pathway.

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Key Words

C-H arylation, 8-hydroxyquinoline, organocatalysis, biaryls, homolytic aromatic substitution

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ID: J66-Y2018