Carbene-catalyzed [3+2+1] annulation via C-N radical coupling of iminyl radicals and ketyl radicals

被引：2
|
作者：
Li, Wenchang [1 ]
Zhou, Peng [1 ]
Zhao, Qing [1 ]
Lin, Kejun [1 ]
Zhu, Tingshun [1 ]
机构：
[1] Sun Yat Sen Univ, Sch Chem, Guangzhou 510006, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 18期
基金：
中国国家自然科学基金;
关键词：
VINYL AZIDES SYNTHESIS; CYCLOPROPANOLS; CYCLIZATION; GENERATION; ACCESS;
D O I：
10.1039/d3ob00468f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An N-heterocyclic carbene-catalyzed cascade [3 + 2 + 1] annulation to assemble vinyl azides, aldehydes, and trihalomethyl reagents (Togni's reagent or CCl4) towards 1,3-oxazin-6-ones was reported. The cascade was triggered by an NHC-catalyzed single electron transfer (SET) between aldehydes and trihalomethyl reagents, followed by the addition of trihalomethyl radicals to vinyl azides, a denitrogenated transformation into iminyl radicals, a C-N radical coupling of iminyl radicals and ketyl radicals, and a base-controlled dehalogenative cyclization.
引用
收藏
页码：3784 / 3788
页数：5
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