Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides

Li-Li Zhang, Yu-Zhong Gao, Sheng-Han Cai, Hui Yu, Shou-Jie Shen, Qian Ping and Ze-Peng Yang ()
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Li-Li Zhang: Tongji University
Yu-Zhong Gao: Shanxi Normal University
Sheng-Han Cai: Tongji University
Hui Yu: Tongji University
Shou-Jie Shen: Shanxi Normal University
Qian Ping: Tongji University
Ze-Peng Yang: Tongji University

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Transition metal-catalyzed enantioconvergent cross-coupling of an alkyl precursor presents a promising method for producing enantioenriched C(sp3) molecules. Because alkyl alcohol is a ubiquitous and abundant family of feedstock in nature, the direct reductive coupling of alkyl alcohol and aryl halide enables efficient access to valuable compounds. Although several strategies have been developed to overcome the high bond dissociation energy of the C − O bond, the asymmetric pattern remains unknown. In this report, we describe the realization of an enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohol (β-hydroxy ketone) and aryl bromide in the presence of an NHC activating agent. The approach can accommodate substituents of various sizes and functional groups, and its synthetic potency is demonstrated through a gram scale reaction and derivatizations into other compound families. Finally, we apply our convergent method to the efficient asymmetric synthesis of four β-aryl ketones that are natural products or bioactive compounds.

Date: 2024
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DOI: 10.1038/s41467-024-46713-x

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