含硼一級胺類化合物之合成及其應用

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Title:	含硼一級胺類化合物之合成及其應用
Other Titles:	Synthesis of boron-containing primary amines and their applications
Authors:	鍾勝烜;Chung, Sheng-Hsuan
Contributors:	淡江大學化學學系碩士班潘伯申
Keywords:	硼;一級胺;boron;peptoid;primary amine;Ugi-4CR;Suzuki reaction;Gabriel reaction
Date:	2013
Issue Date:	2014-01-23 13:46:30 (UTC+8)
Abstract:	本研究成功利用優化之Gabriel reaction合成六個含硼之一級胺類化合物 (Fig. 1)。由於這六個含硼一級胺類化合物皆在溫和的條件下予以合成，因此所得產率皆高於50%以上 (Scheme 1,2)。以含硼一級胺產物為Ugi多組成反應(Ugi-4CR)之起始物並藉由微波輔助條件，本研究成功合成含硼之peptoid衍生物。而這些含硼之peptoid衍生物可藉由一鍋化水解反應，將其轉變為相對應之硼酸化合物 (Fig. 2)。最後，這些Ugi-4CR之peptoids化合物可藉由Suzuki coupling reaction更進一步修飾以達到將結構複雜化的目的 (Fig. 3)。 In this study, the modified Gabriel synthetic condition was developed to build six boron-containing primary amines in good to excellent yields (Fig. 1). This modified condition allowed the synthesis to carry out in mild synthetic processes (Scheme 1,2). Further, the desired boron-containing primary amines were further utilized to construct the peptoid analogs via microwave assisted Ugi four component reaction (Ugi-4CR) (Fig. 2). In addition, these Ugi-4CR boronate esters were converted to the corresponding boronic acids by a one-pot hydration reaction. Finally, the peptoid structures can be further modified by incorporating aryl/heteroaryl component via palladium mediated Suzuki coupling reaction (Fig. 3).
Appears in Collections:	[Graduate Institute & Department of Chemistry] Thesis

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