Modulation of metal species as control point for Ni-catalyzed stereodivergent semihydrogenation of alkynes with water

Yuanqi Wu, Yuhui Ao, Zhiming Li (), Chunhui Liu, Jinbo Zhao, Wenyu Gao, Xuemeng Li, Hui Wang, Yongsheng Liu and Yu Liu ()
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Yuanqi Wu: Changchun University of Technology
Yuhui Ao: Changchun University of Technology
Zhiming Li: Fudan University
Chunhui Liu: Xuchang University
Jinbo Zhao: Changchun University of Technology
Wenyu Gao: Changchun University of Technology
Xuemeng Li: Changchun University of Technology
Hui Wang: Changchun University of Technology
Yongsheng Liu: Changchun University of Technology
Yu Liu: Changchun University of Technology

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract A base-assisted metal species modulation mechanism enables Ni-catalyzed stereodivergent transfer semihydrogenation of alkynes with water, delivering both olefinic isomers smoothly using cheap and nontoxic catalysts and additives. Different from most precedents, in which E-alkenes derive from the isomerization of Z-alkene products, the isomers were formed in orthogonal catalytic pathways. Mechanistic studies suggest base as a key early element in modulation of the reaction pathways: by adding different bases, nickel species with disparate valence states could be accessed to initiate two catalytic cycles toward different stereoisomers. The practicability of the method is showcased with nearly 70 examples, including internal and terminal triple bonds, enynes and diynes, affording semi-hydrogenated products in high yields and selectivity.

Date: 2023
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DOI: 10.1038/s41467-023-37022-w

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