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T. Dao-Huy, B. Waldner, L. Wimmer, M. Schnürch, M.D. Mihovilovic:
"Synthesis of endo- and exo-N-Protected 5-Arylated 2-Aminothiazoles through Direct Arylation: An Efficient Route to Cell Differentiation Accelerators";
European Journal of Organic Chemistry, 2015 (2015), 4765 - 4771.

An improved protocol for the direct arylation of N-phenyl-N-benzyl(thiazol-2-yl)amine by using aryl bromides as aryl donors is reported. The procedure was compared with a previously reported protocol in which aryl iodides were used as arylating agents. The improved direct arylation protocol was applied to structurally isomeric and nonaromatic 3-benzyl-N-phenylthiazol-2(3H)-imine. The two substrates for direct arylation were obtained from a common starting material, Nphenyl(thiazol-2-yl)amine, which was regioselectively benzylated either on the exo-cyclic or the endo-cyclic nitrogen by using two sets of reaction conditions. For the arylation of the isomeric nonaromatic 3-benzyl-N-phenylthiazol-2(3H)-imine, exclusive regioselectivity in the 5-position could be
achieved.

synthetic methods, homogeneous catalysis, arylation, C-H activation

http://dx.doi.org/10.1002/ejoc.201500283