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- Title
Modulation of metal species as control point for Ni-catalyzed stereodivergent semihydrogenation of alkynes with water.
- Authors
Wu, Yuanqi; Ao, Yuhui; Li, Zhiming; Liu, Chunhui; Zhao, Jinbo; Gao, Wenyu; Li, Xuemeng; Wang, Hui; Liu, Yongsheng; Liu, Yu
- 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. Generally, transition metal-catalyzed stereodivergent transfer semihydrogenation of alkynes realized regulation of stereoselectivity by a Z to E isomerization process. Here, authors report a Ni-catalyzed stereodivergent transfer semihydrogenation of alkynes with a base-assisted metal species modulation mechanism, delivering both olefinic isomers smoothly in orthogonal catalytic pathways using cheap and nontoxic catalysts and additives
- Subjects
ALKYNES; METALS; STEREOISOMERS; ISOMERIZATION; ISOMERS; TRANSFER hydrogenation
- Publication
Nature Communications, 2023, Vol 14, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-023-37022-w