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

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

Author keywords

[No Author keywords available]

Indexed keywords

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

EID: 3042739509     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0494634     Document Type: Article
Times cited : (229)

References (199)
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    • These conditions (16 atm of CO together with 5 total atm of air, considering that the autoclave was loaded under 1 atm of air) corresponded to 76.2% of CO in air and were outside the explosion range for CO in air (ca. 17-70% at 18-20 °C and atmospheric pressure, 14.8-71.5% at 100 °C and atmospheric pressure. At higher total pressure, the range of flammability decreases: for example, at 20 atm and 20 °C the range is ca. 20-60%). See: Bartish, C. M.; Drissel, G. M. In Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed.; Grayson, M., Eckroth, D., Bushey, G. J., Campbell, L., Klingsberg, A., van Nes, L., Eds.; Wiley-Interscience: New York, 1978; Vol. 4, pp 774-775.
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    • note
    • 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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    • note
    • 2 in the gaseous mixture further decreases the range of flammability for CO in air: see ref 29.
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    • and references therein
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    • note
    • 2 because we were mainly interested in the formation of urea product and in optimizing its yield and selectivity.
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    • note
    • 2 pressures, with less satisfactory results in terms of yield and selectivity towards ureas.
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    • note
    • 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.
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    • note
    • As we have already pointed out, these conditions are outside the explosion limits for CO-air mixtures (see note 29).


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