光诱导多组分异芳基化 [1.1.1]Propellane 与 Katritzky 吡啶盐。

IF 5.4 3区材料科学 Q2 CHEMISTRY, PHYSICAL

ACS Applied Energy Materials Pub Date : 2024-08-23 Epub Date: 2024-08-14 DOI:10.1021/acs.orglett.4c02571

Yulin Xiao, Jianyang Dong, Yuying Wang, Huijuan Liao, Jiayi Dang, Gang Li, Dong Xue

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引用次数: 0

摘要

(异）芳基双环[1.1.1]戊烷（BCPs）对于构建复杂的类药物靶分子非常重要。在此，我们开发了一种光诱导、Cs2CO3 促进的吡啶鎓 C-N 键均聚裂解方法，用于从氨基酸衍生的 Katritzky 盐中生成烷基自由基，并利用自由基对 [1.1.1]propellane 进行官能化，从而快速生成（杂）芳基化 BCPs。该方法具有优异的官能团耐受性和广泛的底物范围，可用于结构复杂的天然产物的官能化。

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Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane with Katritzky Pyridinium Salts.

(Hetero)arylated bicyclo[1.1.1]pentanes (BCPs) are important for the construction of complex druglike target molecules. Herein, we developed a method for light-induced, Cs₂CO₃-promoted homolytic cleavage of pyridinium C-N bonds for generating alkyl radicals from amino acid-derived Katritzky salts and use of the radicals for functionalization of [1.1.1]propellane to rapidly generate (hetero)arylated BCPs. The method features excellent functional group tolerance and a broad substrate scope and can be used to functionalize structurally complex natural products.

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来源期刊

ACS Applied Energy Materials Materials Science-Materials Chemistry

CiteScore

10.30

自引率

6.20%

发文量

1368

期刊介绍： ACS Applied Energy Materials is an interdisciplinary journal publishing original research covering all aspects of materials, engineering, chemistry, physics and biology relevant to energy conversion and storage. The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrate knowledge in the areas of materials, engineering, physics, bioscience, and chemistry into important energy applications.