Palladium-catalyzed trimerizations of terminal arylalkynes: Synthesis of 1,3-diaryl-2-arylethynyl-1,3-butadienes

被引：25

作者：

Wu, Yao-Ting ^{[1
]}

Lin, Wei-Chih ^{[1
]}

Liu, Chia-Ju ^{[1
]}

Wu, Chuan-Yi ^{[1
]}

机构：

[1] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 11-12期

关键词：

alkynes; cross-coupling; enynes; hydroalkynylation; palladium;

D O I：

10.1002/adsc.200800182

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Various 1,3-diaryl-2-arylethynyl-1,3-butadienes 7 have been prepared by the Pd-catalyzed trimerization of arylalkynes 4. Their structures and stereochemistry have been confirmed by X-ray crystal analyses. This procedure provides high regioselectivity to generate adducts Z-7 in moderate to excellent yields. The scope, limitations and regioselectivity of this reaction have been investigated. In DMSO at 180 degrees C, 1,3-di(1-naphthalenyl)-2-(1-naphthalenylethynyl)-1,3-butadiene (7m) underwent 6 pi-electrocyclization to form 2-(1-naphthalenyl)-3-(1-naphthalenynl-ethynyl)-1,2-dihydrophenanthrene (21). Under acidic conditions, (1Z)-1,3-diphenyl-2-(1-phenylethynyl)-1,3-butadiene (Z-7a) was converted to 1-methyl-3-phenyl-2-(2-phenyl-1-ethionyl)-2-indene (22) in 75% yield.

引用

页码：1841 / 1849

页数：9

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