Issue 4, 2022

Origins of regio- and stereoselectivity in Cu-catalyzed alkyne difunctionalization with CO2 and organoboranes

Abstract

The mechanism and origins of regio- and stereoselectivities of Cu-catalyzed alkyne difunctionalization with CO2 and trialkyl boranes were computationally investigated. The results show that the vicinal addition to alkyne is disfavored due to the kinetical inertness of the alkyl copper intermediate. The favored geminal addition proceeds through the cationic Cu-mediated stereoselective 1,2-migration pathway. The energy decomposition analysis indicates that the σ)(π Pauli repulsion is the dominant factor for controlling the stereoselectivity.

Graphical abstract: Origins of regio- and stereoselectivity in Cu-catalyzed alkyne difunctionalization with CO2 and organoboranes

Supplementary files

Article information

Article type
Research Article
Submitted
29 11 2021
Accepted
08 1 2022
First published
10 1 2022

Org. Chem. Front., 2022,9, 1033-1039

Origins of regio- and stereoselectivity in Cu-catalyzed alkyne difunctionalization with CO2 and organoboranes

L. Hu, H. Gao, Y. Hu, X. Lv, Y. Wu and G. Lu, Org. Chem. Front., 2022, 9, 1033 DOI: 10.1039/D1QO01788H

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