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Charge-Transfer Complex Promoted C-N Bond Activation for Ni-Catalyzed Carbonylation
2017-09-13
Org. Lett. 9(13):3520-3523 Jul 2017

Yu, Hui; Gao, Bao; Hu, Bin; Huang, Hanmin

Abstract:
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.

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