Deacylative Carbon-Carbon Bond Cleavage of Ketone Equivalents: Applications to Radical Carbon-Carbon Bond Formation Reactions

被引：2

作者：

Matsumoto, Akira ^{[1
]}

Nguyen, Bich-Ngoc ^{[2
]}

Honda, Tsubasa ^{[2
]}

Sakamoto, Ryu ^{[2
]}

Huang, Xiao ^{[1
]}

Sakaki, Shigeyoshi ^{[3
]}

Maruoka, Keiji ^{[1
,2
,4
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

[3] Kyoto Univ, Fukui Inst Fundamental Chem, Sakyo Ku, Kyoto 6068103, Japan

[4] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2021年 / 16卷 / 04期

关键词：

oxaziridine; C-C bond cleavage; copper catalysis; alkyl radical; DFT calculation; REDOX-ACTIVE ESTERS; C-C; CARBOXYLIC-ACIDS; ALKYL RADICALS; LIGHT; DECARBOXYLATION; ALDEHYDES; DECARBONYLATION; DERIVATIVES; GENERATION;

D O I：

10.1002/asia.202001366

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This article describes the synthetic application of ketone-derived oxaziridines as alkyl radical precursors in copper-catalyzed Carbon-Carbon bond formation reactions. Experimental and computational studies indicate a free radical mechanism, where alkyl radicals are efficiently generated via cleavage of a Carbon-Carbon bond of oxaziridines. Acyclic and unstrained cyclic oxaziridines are applicable to the present radical process, allowing for the generation of various alkyl radicals with good functional group compatibility.

引用

页码：282 / 286

页数：5