Copper-Catalyzed One-Pot Synthesis of 1,3-Enynes from 2-Chloro-N-(quinolin-8-yl)acetamides and Terminal Alkynes

被引：5

作者：

Zhu, Lifan ^{[1
]}

Guo, Hongyu ^{[1
]}

Feng, Xiujuan ^{[1
]}

Yamamoto, Yoshinori ^{[1
,2
,3
]}

Bao, Ming ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116023, Peoples R China

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

[3] Ritsumeikan Univ, Res Org Sci & Technol, Kusatsu, Shiga 5258577, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 13期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTION; INTERNAL ALKYNES; N-TOSYLHYDRAZONES; PALLADIUM; TRIMERIZATION; ACTIVATION;

D O I：

10.1021/acs.joc.0c01102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the chemo-, regio-, and stereoselective one-pot synthesis of 1,3-enynes is described. The reaction of 2-chloro-N-(quinolin-8-yl) acetamides with terminal alkynes proceeds smoothly in the presence of a copper catalyst at room temperature to produce (E)-1,3-enynes in satisfactory to excellent yields. The mechanism study reveals that the cross-dimerization of internal alkynes generated in situ with terminal alkynes proceeds via allene intermediates. The directing group 8-aminoquinoline plays a key role in the current selective synthesis of (E)-1,3-enynes.

引用

页码：8740 / 8748

页数：9

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