导　　师： 王芒

学科专业： 070303

授予学位： 硕士

作　　者： ;

机构地区： 东北师范大学

摘　　要： Sonogashira反应发现于1975年，在共轭烯炔化合物和取代炔烃等的合成中应用十分广泛。在很多天然化合物、新型材料、农医药以及纳米分子器件的合成中起着十分关键的作用。一般情况下该反应都会采用钯化合物和一价铜化合物来实现催化。近年来人们对Sonogashira反应做了许多的研究和探索，并取得了许多重要进展，实现了Sonogashira反应的进一步优化、绿色化、非Pd催化和无Cu化等等。这些发现使得人们对该反应的了解进一步趋于完善。 我们课题组多年来对二硫缩烯酮有机中间体作了逐步深入和系统的研究。本文在课题组已有成果的基础上，重点以α碘代α羰基二硫缩烯酮为偶连体，探索了不同条件下其与各种端炔的Sonogashira偶联反应，具体研究内容如下： 1、采用新方法高效合成了多种α碘代α羰基二硫缩烯酮。 2、在温和条件下以Pd/(PPh3/)4为催化剂，CuCl为助催化剂实现了α碘代α羰基二硫缩烯酮和各种端炔的Sonogashira偶联反应。拓展了此反应在有机合成领域的运用范围。 3、成功合成了多种具有潜在应用价值的共轭烯炔化合物。 Sonogashira reaction was first reported in1975. It’s an extremely powerful syntheticmethod for the synthesis of conjugated enynes and other important organic intermediates,which often encountered within natural products, molecular materials, pharmaceuticalmolecules or synthetic agrochemicals. The typical Sonogashira reaction usually containspalladium/(0/) as catalyst and copper/(I/) salts as co-catalyst. About this reaction, during the pastfew years, people have made a lot of research and exploration, and obtained some importantachievements. Much advance has been made, but the reaction will still continue to be afast-moving topic in the field of organic chemistry. In the past few years, systematic studies on the ketene dithioacetals and its furtherapplications have been made in our group. Based on the research achievements our grouphave made in the past decades, much new work has been developed in this paper, Especiallywith α-iodo-α-carbonyl ketene cyclic dithioacetals being as the research objects. In order tobetter realize the coupling procedure of α-iodo-α-carbonyl ketene cyclic dithioacetals andterminal acetylenes, precise measurement for more convenient reaction conditions has beenmade in my article. The paper mainly includes the following aspects： /(1/) At room temperature, a new method has been used for the preparationof α-iodo-α-carboxylate ketene cyclic dithioacetals. /(2/) Under the catalysis of Pd/(PPh3/)4along with CuCl as co-catalyst, Sonogashira reactionof α-iodo-α-carbonyl ketene cyclic dithioacetals and terminal acetylenes occurred smoothlyin THF at60℃. /(3/) A series of new conjugated enynes which could have potential values have been madein this paper.

关 键 词： 二硫缩烯酮 碘代脱羧反应 碘代 偶联反应 共轭烯炔

分 类 号： [O643.32]

领　　域： [理学] [理学]