Photoredox-catalyzed multicomponent Petasis reaction in batch and continuous flow with alkyl boronic acids
Monica Oliva, Prabhat Ranjan, Serena Pillitteri, Guglielmo A. Coppola, Monica Messina, Erik V. Van der Eycken, Upendra K. Sharma
Abstract
coupling of an amine, an aldehyde and a boronic acid (BA). Despite its synthetic utility, the inherent drawbacks associated with the traditional two-electron Petasis reaction have stimulated continuous research towards more facile and tolerant methodologies. In this regard, we present the use of free alkyl BAs as effective radical precursors in this MCR through a single-electron transfer mechanism under mild reaction conditions. We have further demonstrated its applicability to photo-flow reactors, facilitating the reaction scale-up for the rapid assembly of complex molecular structures.
Topics & Concepts
Boronic acidChemistryAlkylAmine gas treatingCombinatorial chemistryCatalysisAldehydeFlow chemistryReaction conditionsCoupling reactionContinuous flowOrganic chemistryBiochemical engineeringEngineeringRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesInnovative Microfluidic and Catalytic Techniques Innovation