SCHEDULED MAINTENANCE
A simple N-heterocyclic carbene for the catalytic up-conversion of aldehydes into stoichiometric super electron donors†
Nadhrata
Assani, 
a
Ludivine
Delfau,
b
Preslav
Smits,
b
Sébastien
Redon,
a
Patrice
Vanelle,
a
David
Martin
*b
and
Julie
Broggi
*a
a
Ludivine
Delfau,
b
Preslav
Smits,
b
Sébastien
Redon,
a
Patrice
Vanelle,
a
David
Martin
*b
and
Julie
Broggi
*a
Abstract
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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