Oliva Monica, Ranjan Prabhat, Pillitteri Serena, Coppola Guglielmo Attilio, Messina Monica, Van der Eycken Erik V, Sharma Upendra Kumar
Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven 3001, Belgium.
Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow 117198, Russia.
iScience. 2021 Sep 15;24(10):103134. doi: 10.1016/j.isci.2021.103134. eCollection 2021 Oct 22.
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 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.
多组分反应（MCRs）是以汇聚和原子经济的方式生成各种有机骨架的理想平台。已经开发了许多用于生成高度取代和多样结构的策略，其中，Petasis反应是用于合成取代胺（胺、醛和硼酸（BA）的偶联反应）的可行反应路径。尽管具有合成实用性，但传统双电子Petasis反应的固有缺点促使人们不断研究更简便且耐受性更好的方法。在这方面，我们展示了在温和反应条件下，通过单电子转移机制使用游离烷基硼酸酯作为该多组分反应中有效的自由基前体。我们进一步证明了其在光流反应器中的适用性，便于扩大反应规模以快速组装复杂分子结构。
