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

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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… Click to show full abstract

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.

Keywords: alkenylation arylindazoles; stage ortho; ortho alkenylation; alkenylation; late stage

Journal Title: RSC Advances
Year Published: 2022

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