Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

doi:10.6023/cjoc201211031

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 551-557.DOI: 10.6023/cjoc201211031 Previous Articles Next Articles

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带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成

许晨, 黄鹏程

北京航空航天大学材料科学与工程学院北京 100191

收稿日期:2012-11-15 修回日期:2012-12-14 发布日期:2012-12-18
通讯作者: 黄鹏程 E-mail:huangpc@buaa.edu.cn

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

Xu Chen, Huang Pengcheng

College of Material Science and Technology, Beihang University, Beijing 100191

Received:2012-11-15 Revised:2012-12-14 Published:2012-12-18

1. Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes.PDF(879KB)

Abstract

Using Sonogashira coupling reaction, two kinds of 1,3,5-substituted phenylacetylene dendrimers: 1,3,5-tris[3-(3- hydroxy-3-methyl-1-butynyl)-5-(triisopropylsilylethynyl)phenylethynyl]benzene (B₁) and 1,3,5-tris[3-(trimethylsilylethynyl)- 5-(triisopropylsilylethynyl)phenylethynyl]benzene (B₂) were synthetized and the synthetic routes were compared and discussed. The structures of the target compounds and intermediates were confirmed by ¹H NMR, ¹³C NMR, EI-MS, HRMS techniques and element analysis. In phenylacetylene dendrimers B₁ and B₂, the six terminal acetylene groups on their periphery were protected by two different kinds of groups, respectively. Based on the different deprotection conditions, two different kinds of functional groups could be introduced to B₁ and B₂, respectively.

Key words: phenylacetylene dendrimer, Sonogashira reaction, 1,3,5-tris[3-(3-hydroxy-3-methyl-1-butynyl)-5-(triisopropyl- silylethynyl)phenylethynyl]benzene, 1,3,5-tris[3-(trimethylsilylethynyl)-5-(triisopropylsilylethynyl)phenylethynyl]benzene

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Xu Chen, Huang Pengcheng. Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes[J]. Chin. J. Org. Chem., 2013, 33(03): 551-557.

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带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

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