Organic Letters
Organic Letters
5 years ago

Charge-Transfer Complex Promoted C–N Bond Activation for Ni-Catalyzed Carbonylation

Charge-Transfer Complex Promoted C–N Bond Activation for Ni-Catalyzed Carbonylation
Hanmin Huang, Bao Gao, Bin Hu, Hui Yu
A new strategy was developed for activation of C–N bond via formation of an amine–I2 charge-transfer complex, which facilitates the inert C–N bond activation via oxidative addition with Ni(0). This strategy has been successfully applied in the Ni-catalyzed carbonylation of benzylamines via direct insertion of CO into the C–N bond, which provided a straightforward and rapid approach to arylacetamides in the presence of catalytic amounts of I2 and Ni catalyst. Mechanistic studies suggested that a benzyl radical generated via the oxidative addition was involved in the present reaction.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01488

DOI: 10.1021/acs.orglett.7b01488

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