Copper-Catalyzed Coupling Reactions of Cyclobutanone Oxime Esters with Sulfur Nucleophiles at Room Temperature

被引：27

作者：

He, Mingchuang ^{[1
]}

Yan, Zhaohua ^{[1
]}

Zhu, Fuyuan ^{[1
]}

Lin, Sen ^{[1
]}

机构：

[1] Nanchang Univ, Coll Chem, Nanchang 330031, Jiangxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 24期

基金：

中国国家自然科学基金;

关键词：

C-S; KETOXIME CARBOXYLATES; IMINYL RADICALS; ACETATES; CYCLIZATION; NITRILES; THIOLS; CLEAVAGE; STRATEGY; CASCADE;

D O I：

10.1021/acs.joc.8b02707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed iminyl radical-mediated C-C bond cleavage/cross-coupling tandem reaction of cyclobutanone oxime esters with aryl thiols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature was developed, and aryl cyanopropyl sulfides were smoothly synthesized in 20-88% yields. By altering the copper reagent and the molar ratio of cyclobutanone oxime ester/aryl thiol/DBU, substitutional product N-arylthio cyclo-butanone imines were selectively generated in 50-91% yields. Using this protocol, C-S bond and N-S bond formations using aryl thiols as sulfur sources were realized under very mild conditions without the use of photocatalysis and electrocatalysis techniques.

引用

页码：15438 / 15448

页数：11

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