Methylcarbonate and Bicarbonate Phosphonium Salts as Catalysts for the Nitroaldol (Henry) Reaction
作者： Massimo Fabris , Marco Noè , Alvise Perosa , Maurizio Selva , Roberto Ballini
DOI: 10.1021/JO202294K
关键词: Ionic liquid 、 Phosphonium 、 Bicarbonate 、 Chemistry 、 Nucleophile 、 Steric effects 、 Organic chemistry 、 Catalysis 、 Nitroaldol reaction
摘要: 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 different aldehydes ketones nitroalkanes: not only they allow selective formation nitroaldols but unlock a novel high-yielding access dinitromethyl derivatives ketones.
core.ac.uk
acs.org
unicam.it
sci-hub.se 参考文章(30)
Stuart G. Warren, Anthony J. Kirby, The Organic Chemistry of Phosphorus ,(1967)
Valerie Eta, Päivi Mäki-Arvela, Eero Salminen, Tapio Salmi, Dmitry Yu. Murzin, Jyri-Pekka Mikkola, The Effect of Alkoxide Ionic Liquids on the Synthesis of Dimethyl Carbonate from CO2 and Methanol over ZrO2–MgO Catalysis Letters. ,vol. 141, pp. 1254- 1261 ,(2011) , 10.1007/S10562-011-0666-3
Asit K. Chakraborti, Sudipta Raha Roy, On Catalysis by Ionic Liquids Journal of the American Chemical Society. ,vol. 131, pp. 6902- 6903 ,(2009) , 10.1021/JA900076A
Juan Crugeiras, Ana Rios, Enrique Riveiros, John P. Richard, Substituent Effects on the Thermodynamic Stability of Imines Formed from Glycine and Aromatic Aldehydes: Implications for the Catalytic Activity of Pyridoxal-5′-phosphate Journal of the American Chemical Society. ,vol. 131, pp. 15815- 15824 ,(2009) , 10.1021/JA906230N
Jing Chen, Yi Chen, Yan-Lin Niu, Hua Fu, Yu-Fen Zhao, A carbonyl oxygen migration in electrospray ionization mass spectrometry and its application in differentiating α- and β-alanyl peptides Journal of Mass Spectrometry. ,vol. 37, pp. 934- 939 ,(2002) , 10.1002/JMS.352
Benjamin M. Nugent, Ryan A. Yoder, Jeffrey N. Johnston, Chiral Proton Catalysis: A Catalytic Enantioselective Direct Aza-Henry Reaction Journal of the American Chemical Society. ,vol. 126, pp. 3418- 3419 ,(2004) , 10.1021/JA031906I
Roberto Ballini, Giovanna Bosica, Nitroaldol Reaction in Aqueous Media: An Important Improvement of the Henry Reaction. Journal of Organic Chemistry. ,vol. 62, pp. 425- 427 ,(1997) , 10.1021/JO961201H
Daniele Simoni, Francesco Paolo Invidiata, Stefano Manfredini, Roberto Ferroni, Ilaria Lampronti, Marinella Roberti, Gian Piero Pollini, Facile synthesis of 2-nitroalkanols by tetramethylguanidine (TMG)-catalyzed addition of primary nitroalkanes to aldehydes and alicyclic ketones Tetrahedron Letters. ,vol. 38, pp. 2749- 2752 ,(1997) , 10.1016/S0040-4039(97)00461-9
Santosh K. Mandal, Douglas M. Ho, Milton Orchin, Reaction of electrophiles with manganese(I) and rhenium(I) alkoxide complexes: reversible absorption of atmospheric carbon dioxide Organometallics. ,vol. 12, pp. 1714- 1719 ,(1993) , 10.1021/OM00029A032
Vasile I. Pârvulescu, Christopher Hardacre, Catalysis in ionic liquids Chemical Reviews. ,vol. 107, pp. 2615- 2665 ,(2007) , 10.1021/CR050948H