Decatungstate‐Photocatalyzed Dearomative Hydroacylation of Indoles: Direct Synthesis of 2‐Acylindolines
Thomas Varlet, Damien Bouchet, Elsa Van Elslande, Géraldine Masson
Abstract
We report herein a convenient and scalable dearomative hydroacylation reaction of indoles. Employing readily available aldehydes as the acyl source and TBADT as an inexpensive direct HAT photocatalyst, a variety of indoles derivatives were converted into synthetically interesting 2-acylindolines in good to excellent yields as well as great diastereoselectivity under mild conditions. An asymmetric version of the reaction was successfully developed and an experimental mechanistic investigation was carried out in order to gain further insights on the assumed reaction pathway.
Topics & Concepts
HydroacylationCombinatorial chemistryChemistryScalabilityReaction conditionsOrganic chemistryComputer scienceCatalysisAldehydeDatabaseRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques