A simple N-heterocyclic carbene for the catalytic up-conversion of aldehydes into stoichiometric super electron donors - Archive ouverte HAL
Article Dans Une Revue Chemical Science Année : 2024

A simple N-heterocyclic carbene for the catalytic up-conversion of aldehydes into stoichiometric super electron donors

Nadhrata Assani
Ludivine Delfau
Preslav Smits
Sébastien Redon
Patrice Vanelle
David Martin
Julie Broggi

Résumé

Catalytic amounts of 1,3-di(methyl)imidazole-2-ylidene, one of the simplest and most prototypical N-heterocyclic carbenes, can up-convert aldehydes into powerful stoichiometric sources of electrons (Super Electron Donors) for reductive transformations of iodoaryls (Ered < −2 V). In particular, the hydroarylation of 1,1′-diarylethylenes, which may require high temperatures and inherently generate stoichiometric amounts of oxidized waste, was performed at room temperature, with the concomitant formation of esters as oxidized co-products.

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Chimie
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hal-04688001 , version 1 (04-09-2024)

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Nadhrata Assani, Ludivine Delfau, Preslav Smits, Sébastien Redon, Youssef Kabri, et al.. A simple N-heterocyclic carbene for the catalytic up-conversion of aldehydes into stoichiometric super electron donors. Chemical Science, 2024, 15, pp.14699-14704. ⟨10.1039/d4sc04011b⟩. ⟨hal-04688001⟩
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