本論文研究將分為兩大主題，第一部分我們利用本實驗室所開發較溫和的方法，以DBU(二環[4.3.0]-1, 5-二氮-5-十一烯)促進Seyferth-Gilbert試劑與溴化物進行取代反應，已合成出多樣的α-重氮-β-取代乙基膦酸酯化合物。此反應條件對於官能基的耐受度相當高，不同於以往文獻使用強鹼的條件，此方法能於α-重氮-β-取代乙基膦酸酯的結構上保留較敏感的羰基(如酮、醛、酯)。而在選擇性方面，醛取代的例子顯示溫和的條件使得對溴化物進行取代反應快於Seyferth-Gilbert增碳反應，我們將有效 得到以α-重氮-β-取代乙基膦酸酯化合物為主的產物。
接著，將所合成出的α-重氮-β-取代乙基膦酸酯化合物經由金屬催化劑與苯胺進行氮-氫鍵插入反應以獲得-胺基膦酸酯化合物。此部分主要針對氮-氫鍵插入反應的條件優化探討。經由金屬、溶劑篩選後所得的最佳條件為-重氮--取代乙基膦酸酯與苯胺於甲苯下以銠金屬作為催化劑進行氮-氫鍵插入反應。當我們以鄰甲氧基苯胺取代苯胺所得到的-胺基膦酸酯化合物最終可以經由三氯異氰脲(TCCA)去保護後而得到膦酸酯胺。我們目前已嘗試天冬氨酸所對應的-胺基膦酸酯化合物的去保護反應，而理想的膦酸酯胺化合物目前可以經由萃取後的¹H-NMR光譜中確認獲得。
第二部分為予體/受體類型的重氮乙酸芳基酯與具有酯基/醯胺基的重氮化合物的藍光促進偶聯反應的探討。對於架設藍光促進偶聯反應的裝置方面，我們已嘗試多種不同的裝置提高反應效率，並找出問題加以優化。最後，我們所使用的最佳裝置為將重氮乙酸芳基酯與帶酯基/醯胺基的重氮化合物置於一般試管當中，並以3個5W且波長為450 nm的藍光LED聚光照射整個反應，可以得到理想的三取代雙鍵化合物，而整個反應所需的時間相對於以往的文獻縮短一半，產率相對其他裝置也提升許多。
由整個實驗結果顯示，當予體/受體類型的重氮乙酸芳基酯消耗完畢時，將會剩下許多帶酯基的受體重氮化合物，而以帶醯胺基的受體重氮化合物進行偶聯反應並不會發生此問題。由於本實驗室也合成出許多醯胺基的重氮化合物，我們目前測試了四種不同的官能基(F、Br、OMe、CH₂SEt)。此四種重氮化合物分別對應到各自的紫外-可見分光光度圖譜，如果在可見光區域愈靠近藍光波長450 nm以及具有較大吸收度者，我們推測經藍光照射後可能進行未知的副反應，因而降低三取代雙鍵產物的形成。此外，本身相對敏感的CH₂SEt官能基在此反應中也是能夠順利獲得產物，未來將繼續測試多樣敏感的官能基以及能進行兩端偶聯反應的連接型重氮化合物。

The research would be divided into two themes. In the first part, we have synthesized various α-diazo-β-substituted-ethylphosphonates through the mild condition developed by our laboratory. The method used DBU (1,8-Diazabicyclo[5.4.0]-undec-7-ene) to promote the substitution reaction of Seyferth-Gilbert reagent with bromide compounds. The reaction condition had a high tolerance for functional groups. Different from using strong base condition in the previous literature, our method could retain the more sensitive carbonyl groups such as ketone, aldehyde, and ester, on the structure of α-diazo-β-substituted-ethylphosphonates. In terms of the selectivity, the Sɴ2 substitution reaction was faster than the Seyferth-Gilbert homologation reaction in the case of the benzyl bromide with meta-aldehyde groups. Therefore, we could effectively obtain α-diazo-β-substituted-ethyl-phosphonates under mild condition. Next, the synthesized α-diazo-β-substituted-ethylphosphonates underwent N-H insertion reaction with aniline via rhodium to obtain α-aminophosphonates. When we replace the aniline with 2-methoxyaniline, the α-aminophosphonates could be finally deprotected by trichloroisocyanurate (TCCA) to obtain the amine. We have tried the deprotection reaction of α-aminophosphonates corresponding to aspartic acid. The ideal amine product could only be confirmed by ¹H-NMR spectrum after extraction.
The second part is the synthesis of the blue light-promoted cross-coupling reaction between the aryldiazoacetate (donor/acceptor diazo compound) and the acceptor diazo compound with ester/amide groups to obtain trisubstituted alkene products. We have designed and set up the equipment E of 5W blue LEDs with the wavelength of 450 nm for the blue light-promoted cross-coupling reaction. The time of the reaction was reduced compared to the previous study, and the yield of product was higher with the equipment E. We have demonstrated the reaction of phenyldiazoacetate with amide-substituted diazo compounds with four different functional groups (F, Br, OMe, and CH₂SEt). Based on the individual UV-vis absorption spectrum of the diazo compounds, when the maximum absorbance wavelength in visible region was closer to 450 nm and its absorbance was higher, it may be easily to carry out other side reactions with the irradiation of the blue light. In addition, the functional group of CH₂SEt, which was relatively sensitive, could also successfully obtain products.

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