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Methylcarbonate and Bicarbonate Phosphonium Salts as Catalysts for the Nitroaldol (Henry) Reaction

Author:
Fabris, Massimo, Noè, Marco, Perosa, Alvise, Selva, Maurizio, Ballini, Roberto
Source:
Journal of organic chemistry 2012 v.77 no.4 pp. 1805-1811
ISSN:
1520-6904
Subject:
Lewis bases, aldehydes, anions, bicarbonates, catalysts, catalytic activity, ionic liquids, ketones, nitroalkanes, organic chemistry
Abstract:
Phosphonium ionic liquids exchanged with bicarbonate and methylcarbonate anions (CILs) exhibit catalytic performances comparable to those of sterically hindered (non nucleophilic) organosuperbases such as DBU. At 25–50 °C, under solventless conditions, CILs efficiently catalyze the Henry addition of different aldehydes and ketones to nitroalkanes: not only they allow the selective formation of nitroaldols but they unlock a novel high-yielding access to dinitromethyl derivatives of ketones.
Agid:
5499591