Chromium-catalyzed stereodivergent E- and Z-selective alkyne hydrogenation controlled by cyclic (alkyl)(amino)carbene ligands

Liang Ling, Chenyang Hu, Linhong Long, Xue Zhang, Lixing Zhao, Liu Leo Liu, Hui Chen (), Meiming Luo () and Xiaoming Zeng ()
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Liang Ling: Sichuan University
Chenyang Hu: Southern University of Science and Technology
Linhong Long: Institute of Chemistry, Chinese Academy of Sciences
Xue Zhang: Sichuan University
Lixing Zhao: Sichuan University
Liu Leo Liu: Southern University of Science and Technology
Hui Chen: Institute of Chemistry, Chinese Academy of Sciences
Meiming Luo: Sichuan University
Xiaoming Zeng: Sichuan University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract The hydrogenation of alkynes allows the synthesis of olefins, which are important feedstock for the materials, pharmaceutical, and petrochemical industry. Thus, methods that enable this transformation via low-cost metal catalysis are desirable. However, achieving stereochemical control in this reaction is a long-standing challenge. Here, we report on the chromium-catalyzed E- and Z-selective olefin synthesis via hydrogenation of alkynes, controlled by two carbene ligands. A cyclic (alkyl)(amino)carbene ligand that contains a phosphino anchor enables the hydrogenation of alkynes in a trans-addition manner, selectively forming E-olefins. With an imino anchor-incorporated carbene ligand, the stereoselectivity can be switched, giving mainly Z-isomers. This ligand-enabled geometrical stereoinversion strategy by one metal catalysis overrides common methods in control of the E- and Z-selectivity with two different metal catalysis, allowing for highly efficient and on-demand access to both E- and Z-olefins in a stereo-complementary fashion. Mechanistic studies indicate that the different steric effect between these two carbene ligands may mainly dominate the selective forming E- or Z-olefins in control of the stereochemistry.

Date: 2023
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DOI: 10.1038/s41467-023-36677-9

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