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Published on: November 9, 2019
Chiral cobalt(ii) complex catalyzed Friedel-Crafts aromatization for the synthesis of axially chiral biaryldiols
Chaoran Xu1, Haifeng Zheng, Bowen Hu
1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China. liuxh@scu.edu.cn xmfeng@scu.edu.cn.
Abstract:
An efficient atroposelective synthesis of axially chiral biaryldiols via asymmetric Friedel-Crafts aromatization between p-quinones and 2-naphthols was developed. A chiral cobalt(ii) complex of N,N'-dioxide enabled the process to generate axially chiral biaryldiols in up to 98% yield and 95% ee. A large range of substituents at different positions of p-quinones and 2-naphthols was tolerable. The configuration of the product and the chiral N,N'-dioxide-Co(ClO4)2 catalyst was identified by X-ray crystal diffraction analysis and a possible catalytic model was suggested.
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