Photoinduced decarbonylative borylation of alkyl aldehydes through 4-alkyl-1,4-dihydropyridines,Organic Chemistry Frontiers

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Photoinduced decarbonylative borylation of alkyl aldehydes through 4-alkyl-1,4-dihydropyridines
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2023-12-20 , DOI: 10.1039/d3qo01139a
Chang Lian _{1,

2} , Jianning Zhang _{1,

2} , Fanyang Mo ₁

Affiliation

We propose a novel approach for the facile decarbonylative borylation of aliphatic aldehydes. In this strategy, 1,4-dihydropyridines (DHPs) are synthesized in a single step from the corresponding aldehydes and subsequently reacted with bis(catecholato)diboron to form an alkyl C–B bond through a photoinduced process. Remarkably, this reaction can be conducted under mild conditions and demonstrates compatibility with a wide range of substrates. The experimental findings, in conjunction with density functional theory (DFT) calculations, reveal the involvement of an electron transfer process between the photocatalyst and DHPs. Notably, the appropriate redox properties of DHPs facilitate the generation of alkyl radicals under these conditions, eliminating the need for any external oxidant.

中文翻译：

通过 4-烷基-1,4-二氢吡啶光诱导烷基醛脱羰硼基化

我们提出了一种用于脂肪醛轻松脱羰硼基化的新方法。在该策略中，1,4-二氢吡啶（DHP）由相应的醛一步合成，随后与双（儿茶酚）二硼反应，通过光诱导过程形成烷基C-B键。值得注意的是，该反应可以在温和的条件下进行，并表现出与多种底物的相容性。实验结果与密度泛函理论 (DFT) 计算相结合，揭示了光催化剂和 DHP 之间电子转移过程的参与。值得注意的是，DHP 适当的氧化还原特性有利于在这些条件下生成烷基自由基，从而无需任何外部氧化剂。

更新日期：2023-12-20

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