Efficient synthesis of ureas by direct palladium-catalyzed oxidative carbonylation of amines

Journal of Organic Chemistry

Volumn 69, Issue 14, 2004, Pages 4741-4750

  Gabriele, Bartolo ^a   Salerno, Giuseppe ^a   Mancuso, Raffaella ^a   Costa, Mirco ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; CARBONYLATION; CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL); UREA;

CATALYTIC EFFICIENCIES; NEUROPEPTIDES; PRIMARY AMINES;

AMINES;

AMINE; CARBON DIOXIDE; CARBON MONOXIDE; DIAMINE; DIMETHYL ETHER; ESTER; IODIDE; NEUROPEPTIDE Y5 RECEPTOR; PALLADIUM; POTASSIUM IODIDE; RECEPTOR BLOCKING AGENT; SOLVENT; UNCLASSIFIED DRUG; UREA DERIVATIVE; UREA NEUROPEPTIDE Y5 RECEPTOR ANTAGONIST 972;

AIR; ARTICLE; CARBONYLATION; CATALYSIS; DRUG SYNTHESIS; HIGH TEMPERATURE; OXIDATION; PRESSURE; SOLVATION; STOICHIOMETRY; SYNTHESIS;

AMINES; CARBON; CATALYSIS; OXIDATION-REDUCTION; PALLADIUM; UREA;

EID: 3042739509     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0494634     Document Type: Article

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180. In this reaction, as well as in other cases described subsequently, formation of unidentified heavy products accounted for the difference between the total yield obtained (22%) and substrate conversion (35%).
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190. 2 because we were mainly interested in the formation of urea product and in optimizing its yield and selectivity.
191. 2 pressures, with less satisfactory results in terms of yield and selectivity towards ureas.
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198. Dibutylurea 2a was the only product formed when the reaction was carried out with secondary amines of low nucleophilicity, such as diisopropylamine or N-methylaniline.
199. As we have already pointed out, these conditions are outside the explosion limits for CO-air mixtures (see note 29).