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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.


 

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.


 

 

Publikationsverlauf

Artikel online veröffentlicht:
14. April 2023

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