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摘要：由于P-C键所具有的优异性能，使得含有P-C键的有机膦化合物在有机合成、催化、功能材料以及药物化学等领域受到广泛应用。例如，含有膦酸基团(R-PO(OH)2) 结构的药物被广泛用于糖尿病、心力衰竭、癌症、疟疾、艾滋病。此外，含磷有机阻燃剂，因其无毒无害，并且具有良好的阻燃效果，得到了广泛的研究和使用。近十年来，从过渡金属钯催化到铜催化，再到镍催化，过渡金属催化C-P已受到了深入而广泛的研究，并取得了巨大的成就。但是，传统构建P-C键的方法并不能满足合成具有更多官能团化的有机磷化合物的要求，且对于碳杂键(C-X)的反应研究还不够多。
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本论文首先选择对甲苯磺酰基保护的乙醇胺在对甲苯磺酰氯活化后对磷试剂、硫粉反应作为模型反应来进行构建P-S-C键，选择不同的溶剂、碱、配体、反应温度和反应时间来观察对反应的影响，以此来选取最优的反应条件。通过对反应的条件的筛选，我们发现无催化剂时，以TsOR为原料和S粉、二苯基氢膦反应，在碱Cs2CO3，溶剂H2O和浴温65℃时得到P-S-C键键合的产物。经过磷谱、氢谱、碳谱分析，推测得到了该化合物的结构。通过对反应条件的筛选，最终得到了最优的实验条件。此反应中，选择水作为溶剂是一项有意义的尝试，因为水作为一种绿色无毒的化合物，其作为极性分子能溶解许多极性的有机化合物，也包括无机化合物中盐、酸、碱、酶和过渡金属配合物。该反应模型下P-S-C键的构建为碳杂键（C-X）的构建提供了新思路，并且是绿色化学上的一个很大发现。34163
毕业论文关键词：磷试剂；乙醇胺；P-S-C键构建；最优条件；模型反应
Synthesis of transition metal-catalyzed carbon-heteroatom bond compound
Abstract：Since the phosphorus-carbon has excellent properties such organophosphorus compounds containing phosphorus-carbon bonds in organic synthesis, catalysis, functional materials and medicinal chemistry, and other fields are widely used. For example, containing phosphate groups (RPO(OH)2) the structure of the drug is widely used in diabetes, heart failure, cancer, malaria, AIDS. In addition, phosphorus-containing organic flame retardant, its non-toxic and has good flame retardant effect, has been widely studied and used. Over the past decade, from a catalytic transition metal palladium to copper catalysis, to the nickel catalyst, transition metal catalyzed phosphorus-carbon bond has been a thorough and extensive research, and has made tremendous achievements. However, the conventional way to build phosphorus-carbon bond does not meet the requirements of more functional synthesis of organic phosphorus compound, and the carbon hybrid bond (carbon-heteroatom) reaction studies are not enough.
This paper first choice tosyl protected ethanolamine chloride in toluene after activation of phosphorus reagent, sulfur powder reaction reaction as a model to build phosphorus-sulfur-carbon bonds to select different solvents, bases, ligands, reaction temperature and reaction time to observe the effects on the reaction, in order to select the optimal reaction conditions. By screening of reaction conditions, we have found no catalyst, and sulfur as the raw material powder TsOR, diphenyl hydrogen phosphonate reaction, a base Cesium carbonate, water, and the solvent at a bath temperature of 65 degrees phosphorus-sulfur-carbon bonds together to obtain a product. After phosphorus spectrum, NMR, 13C NMR analysis, suggesting that the structure of the compound obtained. By screening of reaction conditions, and ultimately we get the optimal experimental conditions. This reaction, choose water as a solvent is an interesting attempt, because water as a green non-toxic compound, as polar molecules can dissolve many polar organic compounds, inorganic compounds including salts, acids, bases, enzymes and transition metal complexes. This reaction model phosphorus-sulfur-carbon bonds carbon hybrid bond (carbon-heteroatom) constructed a new idea, and is a great find green chemistry.
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