Iron-catalyzed oxidative C-C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air

被引：24

作者：

Liu, Binbin ^{[1
]}

Cheng, Lu ^{[1
]}

Hu, Penghui ^{[1
]}

Xu, Fangning ^{[1
]}

Li, Dan ^{[2
]}

Gu, Wei-Jin ^{[1
]}

Han, Wei ^{[1
,2
]}

机构：

[1] Nanjing Normal Univ, Sch Chem & Mat Sci, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Jiangsu Key Lab Biofunct Mat,Key Lab Appl Photoch, Nanjing 210023, Jiangsu, Peoples R China

[2] Changsha Univ Sci & Technol, Sch Chem & Biol Engn, Hunan Prov Key Lab Mat Protect Elect Power & Tran, Changsha 410114, Hunan, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 33期

关键词：

C-C-BOND; CARBON-CARBON BOND; AEROBIC OXIDATION; CHEMOSELECTIVE SYNTHESIS; ESTERIFICATION REACTION; PHENYLACETIC ACIDS; HOMOALLYL ALCOHOLS; MOLECULAR-OXYGEN; HYDROXY KETONES; ESSENTIAL OIL;

D O I：

10.1039/c9cc01995b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and selective iron-catalyzed allylic C-C(vinyl) sigma-bond cleavage of allylarenes without the assistance of heteroatoms to give aryl aldehydes is reported. The unstrained carbon-carbon single bond cleavage reaction uses ambient air as the sole oxidant, proceeds efficiently at room temperature, and allows for exceptional functional-group tolerance, which addresses the long-standing challenges of current C-C bond cleavage/functionalization. Notably, the method enables rapid late-stage oxidation of complex bioactive molecules and can be used to expedite syntheses of natural products (vanillin and glucovanillin) from readily available chemical feedstocks.

引用

页码：4817 / 4820

页数：4

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