β-烯氨基羰基化合物的光氧化 C-C 双键裂解：实现胺的选择性 N-甲酰化。

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-11-15 DOI:10.1039/d4ob01688b

Hayeon You, Suk Hyun Lim, Dae Won Cho

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引用次数: 0

摘要

以亚甲基蓝（MB）为光敏剂，对在氮原子的 α 位上具有硅基的缺电子 β-enaminocarbonyl 化合物的 C-C 双键的光氧化裂解进行了探索。光化学生成的 1O2 被添加到 CC 键上，借助系链硅基将其裂解并形成 N-甲酰胺。该反应方案与多种 β-烯氨基羰基底物兼容，包括具有各种 N-烷基、N-苄基和 N-芳基取代基的底物。

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Photooxidative C-C double bond cleavage of β-enaminocarbonyl compounds: toward selective N-formylation of amines.

A photooxidative C-C double bond cleavage of electron-deficient β-enaminocarbonyl compounds possessing a silyl group at the α-position to the nitrogen atom using methylene blue (MB) as the photosensitizer was explored. Photochemically generated ¹O₂ was added across the CC bond with the aid of a tethered silyl group to cleave it and form N-formylamines. This reaction protocol exhibited compatibility with numerous β-enaminocarbonyl substrates, including those with various N-alkyl, N-benzyl and N-aryl substituents.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： The international home of synthetic, physical and biomolecular organic chemistry.