由四炔构筑稠合二苯并硒酚衍生物的环化反应
发布时间:2018-10-15 11:26
【摘要】:环加成构筑新的碳碳键已成为现代合成化学中重要的手段之一。以苯炔中间体为代表的环加成反应在构筑复杂稠环化合物和天然产物有着独特的优势,逐渐成为化学家们研究的热点。本论文系统地探讨了在无催化剂、无氧化剂、无保护条件下四炔底物和二苯基二硒醚参与的HDDA反应研究,反应中避免了中间产物分离过程中带来资源的浪费,属于绿色化学。我们将在无水无氧钯催化条件得到的四炔底物和二苯基二硒醚直接进行反应,得到了稠合苯并硒酚类化合物。该方法简便高效,拥有较好的产率,不需要加入导向基团却有着很好的区域选择性。在反应的过程中经历了一个HDDA历程、一个自由基历程和一个C-H键的活化。在90℃的条件下,用多种取代基(p-F,p-CH_3,p-CH_2CH_3,o-Cl等)的四炔底物与二芳基二硒醚反应,得到了29个含二苯并硒酚骨架的多环化合物。对得到的产物进行了核磁、红外、质谱等手段进行了表征,得到了其中五个产物的X-ray单晶衍射结构。这种方法提供了一个直接、高效、经济的方式构来建稠合二苯并硒酚化合物。
[Abstract]:Cycloaddition to construct new carbon and carbon bonds has become one of the most important methods in modern synthetic chemistry. The cycloaddition reaction represented by the intermediates of phenylacetylene has unique advantages in the construction of complex dense ring compounds and natural products, and has gradually become a hot topic for chemists. In this paper, the HDDA reaction of tetraacetylene substrate and diphenyl diselenide in the presence of no catalyst, no oxidant and no protection has been studied systematically, which avoids the waste of resources in the separation of intermediate products and belongs to green chemistry. In the presence of anhydrous anoxic palladium as catalyst, tetraacetylene substrates and diphenyl diselenides were directly reacted to obtain dense benzo-selenol compounds. The method is simple and efficient, with good yield and good regioselectivity without adding the guided group. During the reaction a HDDA process, a free radical process and a C-H bond activation were observed. At 90 鈩,
本文编号:2272400
[Abstract]:Cycloaddition to construct new carbon and carbon bonds has become one of the most important methods in modern synthetic chemistry. The cycloaddition reaction represented by the intermediates of phenylacetylene has unique advantages in the construction of complex dense ring compounds and natural products, and has gradually become a hot topic for chemists. In this paper, the HDDA reaction of tetraacetylene substrate and diphenyl diselenide in the presence of no catalyst, no oxidant and no protection has been studied systematically, which avoids the waste of resources in the separation of intermediate products and belongs to green chemistry. In the presence of anhydrous anoxic palladium as catalyst, tetraacetylene substrates and diphenyl diselenides were directly reacted to obtain dense benzo-selenol compounds. The method is simple and efficient, with good yield and good regioselectivity without adding the guided group. During the reaction a HDDA process, a free radical process and a C-H bond activation were observed. At 90 鈩,
本文编号:2272400
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