Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 14, Pages 4741-4750Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0494634
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A general synthesis of symmetrically disubstituted ureas and trisubstituted ureas by direct Pd-catalyzed Oxidative carbonylation of primary amines or of a mixture of a primary and a secondary amine, respectively, with unprecedented catalytic efficiencies for this kind of process, is reported. Reactions are carried out at 90-100 degreesC in DME as the solvent in the presence of PdI2 in conjunction with an excess of KI as the catalytic system and under 20 atm of a 4:1 mixture of CO and air. In some cases, working in the presence of an excess of CO2 (40 atm) in addition to CO and air (60 atm total) had a beneficial effect on substrate reactivity and product yield. Cyclic five-membered and six-membered ureas were easily formed from primary diamines. The methodology has been successfully applied to the synthesis of pharmacologically active ureas, such as those deriving from alpha-amino esters or urea NPY5RA-972, a potent antagonist of the neuropeptide Y5 receptor.
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