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A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp2)-H hydroxylation strategy.

ABSTRACT: A diversity-oriented synthesis of bioactive benzanilides via C(sp2)-H hydroxylation has been studied. Different regioselectivity was observed with Ru(ii) and Pd(ii) catalysts. The reaction demonstrates excellent regioselectivity, good tolerance of functional groups, and high yields. A wide range of ortho-hydroxylated-benzanilides can be readily synthesized with excellent regioselectivity via this new synthetic strategy. Computational investigations revealed that the regioselectivity was controlled mainly by both steric and electronic factors. Steric effects determine the regioselective outcomes in the Ru-catalyzed reaction, while electronic effects are dominant in the Pd-catalyzed reaction.

SUBMITTER: Sun YH 

PROVIDER: S-EPMC5975941 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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A diversity-oriented synthesis of bioactive benzanilides <i>via</i> a regioselective C(sp<sup>2</sup>)-H hydroxylation strategy.

Sun Yong-Hui YH   Sun Tian-Yu TY   Wu Yun-Dong YD   Zhang Xinhao X   Zhang Xinhao X   Rao Yu Y  

Chemical science 20151203 3

A diversity-oriented synthesis of bioactive benzanilides <i>via</i> C(sp<sup>2</sup>)-H hydroxylation has been studied. Different regioselectivity was observed with Ru(ii) and Pd(ii) catalysts. The reaction demonstrates excellent regioselectivity, good tolerance of functional groups, and high yields. A wide range of <i>ortho</i>-hydroxylated-benzanilides can be readily synthesized with excellent regioselectivity <i>via</i> this new synthetic strategy. Computational investigations revealed that t  ...[more]

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