Title

利用水楊酸配位基與氯化銅催化碳-氮鍵交互偶合反應之研究

Translated Titles

The study of copper chloride-catalyzed cross-coupling reactions of C-N bond using salicylic acid as a ligand

DOI

10.6845/NCHU.2008.00704

Authors

黃華民

Key Words

交互偶合反應 ; cross-coupling

PublicationName

中興大學化學系所學位論文

Volume or Term/Year and Month of Publication

2008年

Academic Degree Category

碩士

Advisor

陳耀鐘

Content Language

繁體中文

Chinese Abstract

我們以氯化銅與不同的酸根配位基催化碳-氮鍵交互偶合反應,發現以水楊酸的催化效果最佳。此一溫和有效的催化反應系統條件是:10 mol%氯化銅與20 mol% 水楊酸配位基,碳酸銫為鹼, DMF為溶劑,在110℃下反應24小時,進行催化碳-氮鍵交互偶合反應。除了苯胺之外,對於胺類、含氮雜環的芳香化反應,可以得到不錯的產率(55~89%),我們也將此系統應用在Toloxatone的合成應用上,參考文獻報導的合成步驟,在47的醇基不必事先保護條件下,可以直接進行碳-氮鍵交互偶合反應,順利得到產物Toloxatone (32%)。我們也嘗試合成Linezolid的前驅物47b(12%),再經由已知步驟,可得到Linezolid。

English Abstract

We used copper chloride with different acid as ligand to catalyzed C-N bond cross-coupling reaction,and find the salicylic acid has the best catalysis efficiency.The mild and efficient catalyst system is: 10 mol% CuCl2 as copper source, 20 mol% salicylic acid as ligand, Cs2CO3 as base, DMF as solvent,react 24 hours under 110℃ oil bath to catalyzed cross-coupling reaction. Besides aniline,we could obtain good yield (55~89%)for arylation of amines and heterocyclos. We also used the system to synthesize Toloxatone.To compared the process of reference, we could get cross-coupling reaction under the alcohol of 47 was unprotected to obtain Toloxatone(32%).We also tried to synthesize the precursor of Linezolid 47b(12%),and then obtain Linezolid by know procedure.

Topic Category 基礎與應用科學 > 化學
理學院 > 化學系所
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