Copper-catalyzed aerobic oxidative radical alkoxycyclization of tryptamines to access 3-alkoxypyrroloindolines

Abstract

An oxazoline/copper-catalyzed cascade carboamination alkoxylation of substituted tryptamine under mild eco-friendly O2 oxidation conditions was reported.

Branching out: redox strategies towards the synthesis of acyclic α-tertiary ethers

“…In 2021, the authors extended this methodology to the synthesis of the related pyrroloindolines. 115 The proposed mechanism was quite different, implicating Cu-mediated delivery of the pendant amine rather than the generation of free aminyl radicals. Conducting the reactions under an atmosphere of O 2 was shown to increase product yields and it was therefore proposed that O 2 acted as the terminal oxidant, responsible for turning over the copper catalyst and closing the catalytic cycle.…”