Nickel(II)/BINOL-catalyzed enantioselective C–H activation via desymmetrization and kinetic resolution

Qi-Jun Yao, Fan-Rui Huang, Jia-Hao Chen and Bing-Feng Shi ()
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Qi-Jun Yao: Zhejiang University
Fan-Rui Huang: Zhejiang University
Jia-Hao Chen: Zhejiang University
Bing-Feng Shi: Zhejiang University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract The field of nickel catalysis has witnessed remarkable growth in recent years. However, the use of nickel catalysts in enantioselective C–H activation remains a daunting challenge because of their variable oxidation states, intricate coordination chemistry, and unpredictable reactivity patterns. Herein, we report an enantioselective C–H activation reaction catalyzed by commercially available and air-stable nickel(II) catalyst. Readily available and simple (S)-BINOL is used as a chiral ligand. This operationally simple protocol enables the synthesis of planar chiral metallocenes in high yields with excellent enantioselectivity through desymmetrization and kinetic resolution. Air-stable planar chiral nickelacycle intermediates are first synthesized via enantioselective C–H nickelation and shown to be possible intermediates of the reaction. Deuterium-labeling studies, alongside the characterization and transformation of chiral nickel(II) species, suggest that C–H cleavage is the enantio-determining step. Moreover, the large-scale synthesis and diverse synthetic transformations underscore the practicality of this protocol.

Date: 2024
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DOI: 10.1038/s41467-024-51409-3

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