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

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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… Click to show full 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.

Keywords: transfer complex; bond; bond activation; activation; catalyzed carbonylation; charge transfer

Journal Title: Organic letters
Year Published: 2017

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