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Synfacts 2023; 19(05): 0463
DOI: 10.1055/s-0042-1752477
Metals in Synthesis

Highly E- and Z-Selective Hydrogenation of Alkynes Using Chromium and Cyclic Carbene Ligands

Rezensent(en):
Mark Lautens
,
Jonathan Bajohr
Ling L, Hu C, Long L, Zhang X, Zhao L, Liu LL, Chen H, *, Luo M, *, Zeng X. * Institute of Chemistry, Chinese Academy of Sciences, Beijing and Sichuan University, Chengdu, P. R. of China
Chromium-Catalyzed Stereodivergent E- and Z-Selective Alkyne Hydrogenation Controlled by Cyclic (Alkyl)(amino)carbene Ligands.

Nat. Commun. 2023;
14: 990
DOI: 10.1038/s41467-023-36677-9
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Key words

chromium catalysis - hydrogenation

Significance

Achieving stereochemical control in the hydrogenation of alkynes to generate alkenes is a long-standing challenge. Common strategies to synthesize both the E- and Z-olefins selectively from an alkyne utilize two separate metal catalysts. Zeng and co-workers report a ligand-controlled sterodivergent hydrogenation of alkynes using the same metal to access both isomers of the desired alkenes.


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Comment

The authors collect the reaction profile for both ligands. It is noted that the initial formation of the Z-olefins are favored, and in the case of CAAC-P-Cr, product isomerization takes place to yield the E-olefins. This result is due to the less bulky and more electron-rich nature of CAAC-P compared to that of CAAC-N-Cr.


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Publikationsverlauf

Artikel online veröffentlicht:
14. April 2023

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