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Aromaticity-Dependent Regioselectivity in Pd(II)-Catalyzed C–H Direct Arylation of Aryl Ureas

Author:
Jiang, Pingping, Li, Feng, Xu, Yongbao, Liu, Qingwen, Wang, Jing, Ding, Hong, Yu, Renfu, Wang, Qifeng
Source:
Organic letters 2015 v.17 no.23 pp. 5918-5921
ISSN:
1523-7052
Subject:
arylation, catalytic activity, chemical structure, palladium, regioselectivity, urea
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.
Agid:
5789996