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Photoredox-catalyzed multicomponent Petasis reaction in batch and continuous flow with alkyl boronic acids
iScience ( IF 5.8 ) Pub Date : 2021-09-15 , DOI: 10.1016/j.isci.2021.103134
Monica Oliva 1 , Prabhat Ranjan 1 , Serena Pillitteri 1 , Guglielmo Attilio Coppola 1 , Monica Messina 1 , Erik V Van der Eycken 1, 2 , Upendra Kumar Sharma 1
Affiliation  

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.



中文翻译:

光氧化还原催化的多组分 Petasis 反应与烷基硼酸分批和连续流动

多组分反应 (MCR) 是以收敛和原子经济的方式生成各种有机支架的理想平台。高度取代的和多样的结构的产生许多策略已经被开发并在这些当中,petasis反应表示的取代的胺的合成可行的反应歧管通过胺、醛和硼酸 (BA) 的偶联。尽管具有合成效用,但与传统的双电子 Petasis 反应相关的固有缺点刺激了对更简便和耐受性方法的持续研究。在这方面,我们提出了在温和的反应条件下通过单电子转移机制在该 MCR 中使用游离烷基 BA 作为有效的自由基前体。我们进一步证明了它对光流反应器的适用性,促进了复杂分子结构快速组装的反应放大。

更新日期:2021-09-29
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