Photoredox-catalyzed multicomponent Petasis reaction in batch and continuous flow with alkyl boronic acids

Multicomponent reactions (MCRs) are ideal platforms for the generation of a wide variety of organic scaffolds in a convergent and atom-economical manner. Many strategies for the generation of highly substituted and diverse structures have been developed and among these, the Petasis reaction represents a viable reaction manifold for the synthesis of substituted amines via 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.

Authors
Oliva M.1 , Ranjan P.1 , Pillitteri S.1 , Coppola G.A.1 , Messina M.1 , Van der Eycken E.V. 1, 2 , Sharma U.K.1
Journal
Publisher
Elsevier Inc.
Number of issue
10
Language
English
Status
Published
Number
103134
Volume
24
Year
2021
Organizations
  • 1 Katholieke Univ Leuven, Dept Chem, Lab Organ & Microwave Assisted Chem LOMAC, Celestijnenlaan 200F, B-3001 Leuven, Belgium
  • 2 RUDN Univ, Peoples Friendship Univ Russia, Miklukho Maklaya St 6, Moscow 117198, Russia
Date of creation
16.12.2021
Date of change
16.12.2021
Short link
https://repository.rudn.ru/en/records/article/record/77340/
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