Indoles converted to α-perfluoroalkylamino derivatives under mild conditions

What the study found: The study reports a new way to make α-perfluoroalkylamino indole derivatives by sequential perfluoroalkylation and defluoroamination of indoles. The authors state that the method works under mild conditions and gives products in yields up to 80%.
Why the authors say this matters: The authors conclude that this is a versatile and practical strategy for defluorinative functionalization of inert perfluoroalkyl groups. They suggest it opens new avenues for synthesizing structurally diverse heteroarenes, which are ring-shaped compounds containing atoms other than carbon.
What the researchers tested: The researchers tested a sequential transformation on indoles, using sulfinate-derived perfluoroalkyl radicals and hexamethyldisilazane (HMDS), a reagent used here to promote carbon-fluorine bond cleavage and carbon-nitrogen bond formation. They also carried out mechanistic investigations.
What worked and what didn't: The transformation showed good functional group tolerance and afforded a series of valuable α-perfluoroalkylamino indole derivatives. The abstract does not describe specific failures, side reactions, or conditions that did not work.
What to keep in mind: The available summary does not provide detailed scope data, specific substrates, or limitations beyond the stated mild conditions and good functional group tolerance. The mechanistic support is described at a high level only.

Key points

• A new sequential perfluoroalkylation and defluoroamination method was reported for indoles.
• The method was described as mild and tolerant of different functional groups.
• Product yields were reported up to 80%.
• Mechanistic studies supported a cascade involving sulfinate-derived perfluoroalkyl radicals and HMDS-mediated C-F cleavage and C-N bond formation.
• The authors describe the approach as practical for defluorinative functionalization of inert perfluoroalkyl groups.