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  • Title: Aromaticity-Dependent Regioselectivity in Pd(II)-Catalyzed C-H Direct Arylation of Aryl Ureas.
    Author: Jiang P, Li F, Xu Y, Liu Q, Wang J, Ding H, Yu R, Wang Q.
    Journal: Org Lett; 2015 Dec 04; 17(23):5918-21. PubMed ID: 26575848.
    Abstract:
    Palladium-catalyzed C-H direct arylation generally occurs on the ortho-position of directing groups. By comparing meta-arylated products of 2-naphthyl urea to ortho-arylated products of phenyl urea, the ortho- and meta-regioselectivity of aryl ureas were found to depend on the aromaticity of the corresponding aryl substituents. Thus, aromaticity is a new factor which can affect the regioselectivity in C-H direct arylation. The finding was further confirmed by regioselective direct arylation of indole and pyrrole derivatives.
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