One-pot synthesis of unsymmetrical diarylacetylenes via Sonogashira/deacetonation/Sonogashira cross-coupling of two different aryl chlorides with 2-methyl-3-butyn-2-ol

被引：10

作者：

Xu, Kai ^{[1
,2
]}

Sun, Suyan ^{[1
]}

Zhang, Guodong ^{[1
]}

Yang, Fan ^{[1
]}

Wu, Yangjie ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Zhengzhou 450052, Peoples R China

[2] Shangqiu Normal Univ, Coll Chem & Chem Engn, Shangqiu 476000, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 62期

关键词：

SONOGASHIRA REACTIONS; PROPIOLIC ACID; CATALYTIC-SYSTEMS; ROOM-TEMPERATURE; EFFICIENT; ALKYNES; DIARYLALKYNES; BROMIDES; ACETYLENES; HALIDES;

D O I：

10.1039/c4ra02720e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

With the assistance of PdCl2/X-Phos as the catalyst system, a green and efficient protocol for one-pot Sonogashira/Deacetonation/Sonogashira coupling reaction of two different aryl chlorides with 2-methyl-3-butyn-2-ol was developed, affording various unsymmetrical diarylacetylenes in mostly moderate to excellent yields. Note that the cheap and economically available aryl chlorides and 2-methyl-3-butyn-2-ol as the starting materials could be added to the catalyst system directly and simultaneously. Moreover, this tandem reaction could tolerate substrates bearing one or even two ortho-sterically hindered groups and was also applicable to the synthesis of symmetrical diarylacetylenes. In addition, the competitive reaction was performed and a possible mechanism was also proposed.

引用

页码：32643 / 32646

页数：4

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