Tunable Molecular Editing of Indoles with Fluoroalkyl Carbenes

Xihe Bi and Zhaohong Liu describe the tunable molecular editing of indoles.

The rapid generation of molecular complexity through peripheral and skeletal editing of simple starting materials is an important goal of modern chemical synthesis. Indoles are prominent in many therapeutics and bioactive natural products and are abundant in numerous medicinal and agrochemical libraries. Hence, the direct editing of indoles to access new chemical space, higher potency, and improved compound stability or drug-like properties is a central focus of current organic and medicinal chemistry research. “However, existing molecular editing reactions of indoles, such as dearomative cyclization/cycloaddition or C–H functionalization, have mainly focused on the functionalization of the periphery of indoles, leaving the underlying core skeleton intact,” said Professor Xihe Bi from the Northeast Normal University (P. R. of China). Despite some recent advances in the field, existing peripheral and skeletal editing typically rely on different strategies and starting materials. Hence, Professor Bi’s and Dr. Zhaohong Liu’s groups (both at Northeast Normal University) envisioned that a controllable editing process that could edit both the core skeleton and the periphery of the indole scaffold with a common reagent would increase the chemical space around this leading pharmacophore.

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