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

页码：1209 / 1212

页数：4

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