Publication: Synthesis of Ortho-metallated Iridium Complex
for Inter- and Intramolecular Hydroamination of Alkynes and Reductive Amination
| dc.contributor | 劉緒宗 | en |
| dc.contributor.author | Lai, Rung-Yi | en |
| dc.creator | Lai, Rung-Yi | en |
| dc.date | 2007 | en |
| dc.date.accessioned | 2007-11-26T02:34:15Z | |
| dc.date.accessioned | 2018-07-10T05:16:55Z | |
| dc.date.available | 2007-11-26T02:34:15Z | |
| dc.date.available | 2018-07-10T05:16:55Z | |
| dc.date.issued | 2007 | |
| dc.description.abstract | A series of P~N ligands (o-(diphenylphosphino)(N-benzylidene)- aniline) were prepared by the acid catalyzed condensation of 2-(diphenylphosphino)- aniline with the corresponding aldehydes or ketones. Reaction of ligand La~Ld with [Ir(COD)Cl]2 provided the substitution product [(P-(LX)Ir(COD)Cl](X= a. b. c. d) (13a~13d). Treatment of 13a with AgBF4 yielded the cyclometalled iridium hydride complex [P,N,C-(P~N)Ir(COD)H]BF4 (14). Carrying out the substitution of [Ir(COD)Cl]2 with 13a under atmospheric pressure of CO resulted in the formation of [P,N,C-(P~N)IrH(CO)Cl] (15). Conversion of 3 into 4 can also be achieved by the substitution reaction of 14 with CO in presence of tetraethylammonium chloride. Moreover, treatment of 14 with triphenylphosphine and tetraethylammonium bromide under atmospheric pressure of CO resulted in the formation of [P,N,C-(P~N)Ir(CO)(PPh3)H] (16). However, carrying out the substitution of [Ir(COD)Cl]2 with Lb under atmospheric pressure of CO resulted the formation of [P,N,O-(P~N)Ir(CO)HCl] (17). Finally, treatment of 13d with NaB[3,5-C6H3(CF3)2]4 (denoted as NaBArF4) afforded [(P~N)Ir(COD)]BArF4 (18) without the formation of C-H activation product due to the steric effect. All iridium complexes were not good catalysts for hydroamination. However, the combination of 15 with NaBArF4 provided a good catalytic system for both intra- and intermolecular hydroamination of alkynes. Further, in the presence of NaBArF4 acting as Bronsted acid, complex 15 show an excellent activity on reductive amination of aldehydes in water. | en |
| dc.description.tableofcontents | 目錄 I 附圖目錄 III 附表目錄 IV 論文摘要（中文） V 論文摘要（英文） VI 第一章 緒論 1 第1-1節 環金屬化反應（Cyclometallation） 1 第1-2節 分子內與分子間胺化反應 (Hydroamination) 5 第1-3節 還原胺化反應（Reductive amination） 9 第1-4節 研究目的 11 第二章 環銥化金屬錯合物之合成 13 第2-1節 配位基之合成 13 第2-2節 合成膦配位之銥金屬錯合物 15 第2-3節 環銥化反應（配位基La） 18 第2-4節 配位基Lb、Lc與銥金屬的配位研究 23 第2-5節 配位基Ld與銥金屬的配位研究 27 第三章 環銥化金屬錯合物在胺化反應的應用 30 第3-1節 分子內胺化反應 30 第3-2節 分子間胺化反應 37 第3-3節 反應機構的討論 39 第四章 還原胺化反應 41 第4-1節 還原胺化反應 41 第4-2節 Syntheis of Primary Amines by Using Reductive Amination 45 第4-3節 反應機構的討論 47 第五章 結論 49 第六章 實驗部分 51 第6-1節 測試及實驗儀器 51 第6-2節 試劑來源與前處理 52 第6-3節 實驗過程 53 第6-4節 化合物之製備 53 參考文獻 81 附錄I 部分化合物之NMR光譜 91 附錄II 晶體結構圖 112 | zh_TW |
| dc.identifier | zh-TW | en |
| dc.identifier.uri | http://ntur.lib.ntu.edu.tw//handle/246246/51766 | |
| dc.language | zh-TW | en |
| dc.language.iso | en_US | |
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[94] (a) Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527. (b) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. | en |
| dc.subject | 環銥化金屬錯合物 | en |
| dc.subject | 催化 | en |
| dc.subject | cyclometallated iridium complex | en |
| dc.subject | hydroamination | en |
| dc.subject | reductive amination | en |
| dc.title | Synthesis of Ortho-metallated Iridium Complex for Inter- and Intramolecular Hydroamination of Alkynes and Reductive Amination | en |
| dc.type | thesis | en |
| dspace.entity.type | Publication |