DOI:
10.1055/s-00000083
Synlett
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The ratio of amines has a clear impact on the selectivity of the reaction. In the case of oxidative carbonylation of 4-fluoroaniline (1m) and aniline (1n), when the ratio is 1:1, the unsymmetrical urea 2ma was obtained in 62% yield, accompanied with a 30% yield of a symmetrical urea 2m from 4-fluoroaniline. Further increasing the ratio to 1:2 resulted in enhancing the selectivity (2ma: 78% yield; 2m: 15% yield). When the ratio is 1:4, 2ma can have a high yield (87%) and selectivity (2m: less than 5% yield). If 1m is used in excess, the main product is 2m: Zhang C, Jiao N.
Angew. Chem. Int. Ed. 2010;
49: 6174
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