Construction of 3-Oxazolin-5-one via Visible Light-Induced Nondecarboxylative Coupling and Sequential Reactions

被引：3

作者：

Ma, Shanshan ^{[1
]}

Cao, Haoying ^{[1
]}

Gao, Rongwan

Feng, Yanhong ^{[1
]}

Guo, Yawen ^{[1
]}

Guan, Wei ^{[2
]}

Duan, Xinfang ^{[1
]}

Jiao, Peng ^{[1
]}

机构：

[1] Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China

[2] Northeast Normal Univ, Fac Chem, Changchun 130024, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 12期

关键词：

ELECTROCHEMICAL-BEHAVIOR; ALPHA-NITROALKYLATION; PHOTOREDOX CATALYSIS; NITRILE YLIDES; ARYLATION; PHOTOREACTIONS; REARRANGEMENT; NITROALKANES; OXIDATION; ANIONS;

D O I：

10.1021/acs.orglett.3c00469

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Oxazolin-5-ones are precursors of nitrile ylides and represent valuable 1,3-dipoles for constructing cyclic imines or pyrrole compounds. Harnessing the power of photocatalysis, we accomplished a straightforward synthesis of 3-oxazolin-5-ones from redox-active esters and secondary nitro compounds. Visible light-induced nondecarboxylative coupling of a redox-active ester, nitro aldol condensation, and subsequent visible light-induced N-oxide deoxygenation were accomplished within 2 h. The reaction mechanism was supported by experimental data and DFT calculations.

引用

页码：2098 / 2102

页数：5

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