Copper-Catalyzed Synthesis of Tetrasubstituted Allenes from Quaternary Ammonium Salts and Grignard Reagents

被引：12
作者：
Ma, Shengming [1 ,2 ]
Liu, Qi [1 ]
Tang, Xinjun [1 ]
Cai, Yujuan [1 ]
机构：
[1] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
[2] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 6卷 / 09期
基金：
中国国家自然科学基金;
关键词：
allenes; ammonium salts; copper; cross-coupling reactions; Grignard reagents; ENANTIOSELECTIVE SYNTHESIS; ALDOL REACTION; PROPARGYL CARBOXYLATES; ASYMMETRIC-SYNTHESIS; CARBINOL ALLENOATES; SUBSTITUTED ALLENES; 2+2+2 CYCLOADDITION; COUPLING REACTIONS; ORGANIC-SYNTHESIS; CHIRAL ALLENES;
D O I：
10.1002/ajoc.201600620
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Although the synthesis of allenes has made considerable progress, methods for tetrasubstituted allenes are still limited. In this paper, the CuBr2-catalyzed cross-coupling reaction of Grignard reagents and propargylic ammonium salts in tetrahydrofuran at 60 degrees C under argon delivered tetrasubstituted allenes in good to excellent yields. The reaction is thought to proceed by an S(N)2' pathway.
引用
收藏
页码：1209 / 1212
页数：4
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