Catalysis of Ugi four component coupling reactions by rare earth metal triflates

Journal of Organic Chemistry

Volumn 73, Issue 14, 2008, Pages 5595-5597

  Okandeji, Babajide O ^a   Gordon, Jonathan R ^a   Sello, Jason K ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; CHEMICAL REACTIONS; METALS; NITROGEN COMPOUNDS; NONFERROUS METALS; ORGANIC COMPOUNDS; RARE EARTH ELEMENTS; SCANDIUM; SUGAR (SUCROSE); YTTERBIUM;

AMERICAN CHEMICAL SOCIETY (ACS); AROMATIC ALDEHYDES; CHEMICAL EQUATIONS; COU PLING REACTIONS; IMINE INTERMEDIATE; MULTICOMPONENT REACTION (MCR); RARE EARTH METAL TRIFLATES; REACTION YIELDS; YTTERBIUM(III) TRIFLATE;

CHEMICAL BONDS;

ALDEHYDE DERIVATIVE; IMINE; LANTHANIDE; SCANDIUM; SULFONIC ACID DERIVATIVE; YTTERBIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; QUANTITATIVE ANALYSIS; STOICHIOMETRY;

EID: 48249113283     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800745a     Document Type: Article

References (26)

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21. 3 facilitate unproductive reaction of aldehydes with nucleophilic solvents like methanol and trifluoroethanol.
22. A survey of catalyst loadings revealed that 10 mol% is optimal (see Supporting Information).
23. 2.
24. Cyclohexylisocyanide is reported to be slightly more reactive than benzyl isocyanide in Ugi 4CC reactions: Portal, C.; Launay, D.; Merritt, A.; Bradley, M. J. Comb. Chem. 2005, 7, 554,
25. 3 enhanced the rate of imine formation under these conditions. See Supporting Information.
26. Precondensation of the aldehyde and the imine is reported to improve the yield of Ugi 4CC reactions. See ref 2.