Access to 2-substituted-2H-indazoles via a copper-catalyzed regioselective cross-coupling reaction

Organic & Biomolecular Chemistry
Rong ZhangXianhua Pan

Abstract

A CuCl catalyzed C-N cross-coupling reaction using commercially available 1H-indazoles with diaryliodonium salts is described. The methodology features ample structural versatility, affording 2-substituted-2H-indazole in good yields and complete N(2)-regiocontrol. Furthermore, the utility of the reaction was demonstrated in the synthesis of a known estrogen receptor β agonist. Mechanistic studies using density functional theory calculations suggested that the complete regioselectivity can be attributed to the only weak base TfO- in our system which could not deprotonate indazoles, and the catalyst oxidation process would be the rate-determining step.

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Citations

Sep 25, 2019·Organic & Biomolecular Chemistry·Yan-Ling LiuJian-Zhong Chen
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Karen Rodríguez-VillarJaime Pérez-Villanueva

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