4.6 Article

Late-stage ortho-C-H alkenylation of 2-arylindazoles in aqueous medium by Manganese(i)-catalysis

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RSC ADVANCES
卷 12, 期 30, 页码 19412-19416

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ra03547b

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  1. SERB, New Delhi [CRG/2020/000362]
  2. CSIR-New Delhi

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This study describes an Earth-abundant and water-tolerant manganese(I)-catalyzed alkenylation reaction via C-H bond activation with a unique level of E-selectivity. The reaction proceeds by controlling the C3 nucleophilicity of 2-aryl indazoles. This method is applicable to the late-stage functionalization of complex molecules.
Earth-abundant and water-tolerant manganese(i) catalyzed alkenylation of 2-arylindazole with alkyl and aryl alkynes through C-H bond activation is described with a unique level of E-selectivity. The reaction proceeds through the control of C3 nucleophilicity of 2-aryl indazoles. This method is applied to the late-stage functionalization of complex molecules including ethinylestradiol, norethisterone, and N-protected amino acid derivatives. The kinetic isotope studies suggest that the C-H bond activation step may not be the rate-determining step.

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