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研究生:張永宏
研究生(外文):Yung-Hung Chang
論文名稱:含氮雜環碳烯金屬錯合物之合成、性質及應用
論文名稱(外文):Synthesis, Properties and Application of N-Heterocyclic Carbene Metal Complexes
指導教授:劉緒宗
指導教授(外文):Shiuh-Tzung Liu
學位類別:碩士
校院名稱:國立臺灣大學
系所名稱:化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:中文
論文頁數:124
中文關鍵詞:含氮雜環碳烯銥金屬雙鈀金屬
外文關鍵詞:N-heterocyclic carbeneiridiumdinuclear palladium
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本篇論文中,我們探討飽和及未飽和含氮雜環碳烯銥金屬錯合物在催化活性、碳烯-金屬化學鍵的穩定性以及配位化學上的差異。藉由在咪唑的氮上修飾苯甲基為取代基的銥金屬碳烯錯合物來加以闡述。
藉由金屬碳烯轉移反應,我們成功地將未飽和含氮雜環碳烯從銀金屬轉移至銥金屬前驅物[Ir(COD)Cl]2,接著通入一氧化碳來取代弱配位性的環辛二烯而得到順式的cis-[(IBn)Ir(CO)2Cl]。另外,也藉由(SIBn)W(CO)5與 [Ir(COD)Cl]2作用,成功將碳烯轉移至銥金屬上,而直接合成出[(SIBn)Ir(CO)2Cl]。當膦化物與上述的 [(NHC)I(CO)2Cl]反應時,膦化物會取代反式位置上的CO取代基而形成[(NHC)Ir(CO)(PR3)Cl]。由X光單晶繞射分析鑑定,顯示[(IBn)Ir(CO)(PR3)Cl]與[(SIBn)Ir(CO)(PR3)Cl]上的碳烯與銥金屬鍵長相當。並且從光譜分析及晶體結構數據發現[(NHC)Ir(CO)(PR3)Cl]的錯合物與Vaska’s 錯合物相當類似。因此,我們推論其含氮雜環碳烯與膦化物在ㄧ價銥金屬上有相似的配位能力。此外,將所合成出來的銥金屬錯合物應用在N-alkylation催化反應上,其係經由氫轉移反應來成功得到二級胺化物。從催化反應的結果來看,未飽和與飽和碳烯銥金屬錯合物在催化活性上並沒有引人注目的差異,但是(SIBn)Ir(CO)(PR3)Cl還是比其他銥金屬錯合物有稍好的活性。
另一方面,成功合成出2,7-bis(1-mesitylimidazolium-3-yl)naphthyridine鹽類,相同地經由金屬碳烯轉移反應,將這多螯合型配位基的銀錯合物與Pd(PhCN)Cl2反應,在CH3CN為溶劑下,可以得到雙分子鍵結型態的含氮雜環碳烯二價鈀金屬錯合物,並且探討此錯合物結構。
In this thesis, we have synthesized both saturated and unsaturated N-heterocyclic carbene iridium complexes [(NHC)Ir(CO)2Cl] (where NHC = IBn, SIBn) and have studied the difference between these complexes on coordination behavior, stability and catalytic activity. The unsaturated carbene complex cis-[(IBn)Ir(CO)2Cl] was prepared via the carbene transfer from the corresponding silver carbene complex to [Ir(COD)2Cl]2 followed by the ligand substitution with CO, whereas the saturated one cis-[(SIBn)Ir(CO)2Cl] was obtained directly via the carbene transfer from (SIBn)W(CO)5. Treatment of phosphines with [(NHC)Ir(CO)2Cl] resulted the formation of the products with the phosphine ligand trans to the carbene moiety via substitution of CO. X-ray structural determinations show that the distances of Ir-C(carbene) in both [(IBn)Ir(CO)(PR3)Cl] and [(SIBn)Ir(CO)(PR3)Cl] are essentially the same. Analyses of spectroscopic and crystal structural data of iridium complexes (NHC)Ir(CO)(PR3)Cl and the Vaska’s complex reveal that NHC ligands and phosphines have a similar donating ability toward Ir(I) metal center. All iridium complexes studied in this work are good pre-catalysts on N-alkylation of amines with alcohols via hydrogen transfer reduction. It appears no dramatic difference on the catalytic activity among these iridium carbene complexes; but the saturated carbene complex SIBn-Ir(CO)(PR3)Cl appears to be slightly more active.
On the second project, 2,7-bis(1-mesitylimidazolium-3-yl)naphthyridine salt was used as a carbene precursor, which reacted with Ag2O to yield the corresponding silver carbene complex. Treatment of this silver complex with Pd(PhCN)2Cl2 in CH3CN yielded the dimeric NHC-Pd(II) complex. Structural determination of the palladium complex was discussed.
目錄 I
附圖目錄 III
附表目錄 IV
附圖(Scheme)目錄 V
論文摘要 (中文) VI
論文摘要 (英文) VII
第一章 緒論 1
第一節 碳烯的簡介 1
第二節 含氮雜環碳烯金屬錯化合物 2
第三節 含氮雜環碳烯金屬錯合物的應用 3
第四節 含氮雜環碳烯銥金屬錯合物及應用 5
第五節 含氮雜環碳烯雙金屬錯合物 9
第六節 實驗目的 12
第二章 含氮雜環碳烯銥金屬錯合物的合成 13
第一節 苯甲基取代含氮雜環碳烯銥金屬錯合物之合成 13
第二節 含氮雜環碳烯銥金屬含膦錯合物之合成 20
第三節 含氮雜環碳烯銥金屬含雙膦錯合物之合成 25
第三章 含氮雜環碳烯銥金屬錯合物之配位化學探討 29
第一節 含氮雜環碳烯銥金屬錯合物與硫、三氟醋酸之反應 29
第二節 含氮雜環碳烯銥金屬錯合物與銀試劑、一氧化碳之反應 32
第三節 含氮雜環碳烯銥金屬錯合物與螯合型膦化物配位基之反應 37
第四節 含氮雜環碳烯銥金屬含環辛二烯配位錯合物之配位化學探討 39
第四章 銥金屬碳烯錯合物之催化反應探討 42
第一節 催化條件的最佳化 42
第二節 其他醇類及胺類之N-烷基化反應 46
第三節 吲哚及其衍生物之合成 50
第五章 結論 53
第六章 實驗部分 54
第一節 實驗儀器 54
第二節 試劑來源與反應前處理 55
第三節 實驗過程 55
第四節 化合物的製備 56
參考文獻 73
附錄 I含氮雜環碳烯雙鈀錯合物之合成與鑑定 81
附錄 II 部分化合物之NMR光譜及質譜 87
附錄 III 晶體結構圖 111
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