Copper-Mediated C4─H Selective Fluoroalkoxylation of Indoles via a Transient Directing Group Strategy

Ming-Shun Mei; Yanghui Zhang

doi:10.1002/cjoc.70310

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) :3630 -3636. DOI: 10.1002/cjoc.70310

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Copper-Mediated C4─H Selective Fluoroalkoxylation of Indoles via a Transient Directing Group Strategy

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Abstract

Fluoroalkoxylated heterocycles, such as indoles, holds significant importance in pharmaceuticals and biology. Herein, we report a copper-mediated C4–H fluoroalkoxylation reaction of indoles via a transient directing group (TDG) strategy. This reaction exhibits excellent regioselectivity and broad functional group compatibility, offering a new approach for the synthesis of fluoroalkoxylated indoles. The reaction also represents an unprecedented example of 3d-transition metal-catalyzed C─H fluoroalkoxylation via a TDG strategy.

Keywords

Transient directing group / Copper / C—H activation / Fluoroalkoxylation / Indoles / Regioselectivity / HFIP / Imines / Aldehydes / Amino acids / N-Heterocycles

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Ming-Shun Mei, Yanghui Zhang. Copper-Mediated C4─H Selective Fluoroalkoxylation of Indoles via a Transient Directing Group Strategy. Chinese Journal of Chemistry, 2025, 43(24): 3630-3636 DOI:10.1002/cjoc.70310