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1.1.5.1.1.3 Use of Urea and Guanidine Directing Groups

DOI: 10.1055/sos-SD-217-00074

Dornan, P. K.; Dong, V. M.Science of Synthesis: Catalytic Transformations via C—H Activation, (20151161.

While performing a mechanistic study on regioselectivities obtained in the vinylation of substituted anilides, Brown and co-workers found that urea substrates are more reactive than the corresponding anilides (Scheme 6).[‌23‌] They compared a series of challenging electron-poor arylureas 10 with literature data for the corresponding anilides using 5 mol% palladium[‌12‌] and found that comparable or slightly higher yields of products 12 could be obtained with only 2 mol% palladium.

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References


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