1,7-二芳基-1,6-庚二炔化合物的合成
收稿日期: 2014-08-20
修回日期: 2014-10-16
网络出版日期: 2014-11-13
基金资助
国家自然科学基金(No. 21172076)资助项目.
Synthesis of 1,7-Diarylhepta-1,6-diyne Compounds
Received date: 2014-08-20
Revised date: 2014-10-16
Online published: 2014-11-13
Supported by
Project supported by the National Natural Science Foundation of China (No. 21172076).
1,6-庚二炔是有机合成的重要中间体, 我们以PdCl2/CuI为催化剂, NEt3为碱, 在四氢呋喃溶剂中实现了二炔与卤代芳烃Sonogashira偶联反应, 合成了10个1,7-二芳基-1,6-庚二炔化合物, 该方法也适用于二卤芳烃如1,8-二碘萘与末端炔偶联合成1,8-二苯乙炔基萘. 所有合成的目标化合物结构经1H NMR, 13C NMR, IR 和MS表征.
关键词： 钯催化; 1,6-庚二炔; Sonogashira反应
温燕梅 , 谢建英 , 冯润光 , 黄绪明 . 1,7-二芳基-1,6-庚二炔化合物的合成[J]. 有机化学, 2015 , 35(3) : 735 -738 . DOI: 10.6023/cjoc201408021
Hepta-1,6-diynes are very useful synthetic intermediates. Using PdCl2/CuI as the catalyst and NEt3 as the base in tetrahedrofuran, ten 1,7-diarylhepta-1,6-diynes were synthesized by a simple Sonogashira coupling reaction of terminal diacetylenes and aryl halides. It is also indicated that 1,8-diiodonaphthalene can undergo the same transformation to 1,8- bis(phenylethynyl)naphthalene under typical conditions. Moreover, the structures of hepta-1,6-diyne derivatives were confirmed by 1H NMR, 13C NMR, IR and MS techniques.
Key words： Palladium-catalyzed; Hepta-1,6-diyne; Sonogashira reaction
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