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Synthesis of urea derivatives

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Chan-Lam Coupling


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The arylation of N-H and O-H containing compounds at room temperature with phenylboronic acids is promoted in the presence of cupric acetate and a tertiary amine. Substrates include phenols, amines, anilines, amides, imides, ureas, carbamates, and sulfonamides.
D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winteres, Tetrahedron Lett., 1998, 39, 2933-2936.


Imidazolidin-2-ones are prepared in two steps from readily available N-allylamines. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-ones with generation of two bonds and up to two stereocenters in the presence of aryl bromides, a catalytic amount of Pd2(dba)3/Xantphos and NaOtBu.
J. A. Fritz, J. S. Nakhla, J. P. Wolfe, Org. Lett., 2006, 8, 2531-2534.