Chiral Copper Complex-Catalyzed Enantioselective Oxidative Cross-Coupling of 2-Naphthols for Synthesis of
Jia-Xu Wen1, Fei Chen1, Chunbo Bo1
1School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, North 4th Road, Shihezi 832003, China.
Abstract:
An efficient Cu-Box system was developed for the oxidative cross-coupling of 2-naphthols under mild conditions. The method tolerates a broad substrate scope, and a series of C1-symmetric chiral BINOLs were obtained in excellent yields (up to 96%) and enantioselectivities (up to a 98:2 e.r.). By combining electron-rich and electron-deficient 2-naphthols to create a significant redox potential difference between the two reaction partners, the challenge of chemoselectivity was addressed, driving preferential cross-coupling over homocoupling. DFT calculations and HRMS analyses revealed a radical-mediated pathway for this transformation.
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