A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5 + 2] cycloaddition redox intermediates - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Green Chemistry Année : 2020

A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5 + 2] cycloaddition redox intermediates

Résumé

A bioinspired organocatalytic cascade reaction mimicking both purpurogallin biosynthesis and copper amine oxidases (CuAOs) activity is described, at room temperature under ambient air, for the activation of the α-C–H bond of primary amines. The reaction sequence uses low-cost commercially available pyrogallol as a precatalyst which undergoes an in situ oxidative self-processing step, resulting in its conversion into natural purpurogallin, a [5 + 2] cycloaddition redox intermediate. This is further involved in the CuAOs-like transamination mechanism for producing, under single turnover, the active biomimetic organocatalyst which mediates the selective oxidative coupling of primary amines, including the non-activated substrates of CuAOs. Without any metal cocatalyst or additives, the protocol gives access to cross-coupled imines as well as 1,2-disubstituted benzimidazoles. The isolation of not easily accessible [5 + 2] cycloaddition redox intermediates provides direct and clear evidence for the proposed dual biomimetic process.
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Dates et versions

hal-02491888 , version 1 (09-11-2020)

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Martine Largeron, Patrick Deschamps, Karim Hammad, Maurice-Bernard Fleury. A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5 + 2] cycloaddition redox intermediates. Green Chemistry, 2020, 22 (6), pp.1894-1905. ⟨10.1039/c9gc03992a⟩. ⟨hal-02491888⟩
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