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Article Dans Une Revue Chemistry - A European Journal Année : 2012

Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction

Résumé

The α-alkylation of imines is a valuable carbon-carbon bondforming strategy which is still an underdeveloped area, [1-3] despite the synthetic potential of its α-branched imine products. 4 The direct C-H bond functionalization of imines with alkyl halides has proven challenging due to competing side reactions, such as Mannich condensation, N-alkylation and hydrolysis. [1,5] The indirect approach based on the intermolecular nucleophilic alkylation reaction of enamine [6] or enamide [7] derivatives was not found more efficient. Moreover, the only corresponding products reported were α-alkylated carbonyl compounds. [8] To the best of our knowledge, there is no efficient method for the preparation of α-alkylated imines. In this communication, we disclose a novel αalkylation reaction of imines which can be achieved by photoredox-mediated direct intermolecular C−H functionalization of enamide derivatives, involving a radical-cationic domino process.

Domaines

Chimie organique
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Dates et versions

hal-04046908 , version 1 (27-03-2023)

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Thibaut Courant, Géraldine Masson. Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction. Chemistry - A European Journal, 2012, 18 (2), pp.423-427. ⟨10.1002/chem.201103062⟩. ⟨hal-04046908⟩
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