茂型后过渡金属配合物促进的C-H键活化反应研究
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摘要
本文研究了多个系列茂型后过渡金属化合物促进的C-H键活化计量和催化反应,这些结果有助于我们进一步理解C-H键活化机理和促进在有机合成中的应用。
发展了一类茂铑化合物催化的串联氧化环化反应,能高效地合成萘并[1,8-bc]吡喃衍生物。该反应的发生经过了连续的sp2C-H键/sp3C-H键和sp2C-H键/O-H键的断裂,而且两步与不对称炔烃的环化反应都具有高度区域选择性。进一步实验表明炔烃插入是一个分步的过程,而1-萘酚衍生物是一个中间体。得到的大部分萘并[1,8-bc]吡喃产物都展示出了较强的固态荧光性质。
研究了(η5-C5Me5)Ir(CO)2苯溶液的光照C-H键活化以及随后在空气中的氧化反应,得到了一个单核铱化合物、三个双核铱化合物和一个结构新颖的六核铱簇合物,而且我们进一步研究了所得部分化合物的反应性和相互转换关系,并对这些化合物形成机理做了进一步分析。
制备了一系列桥连茂型铱碘桥聚合物{(C5Me4)(CH2)n(C5Me4)(IrI2)2},m (n=2-4),并以它们为起始原料合成了一系列双核铱化合物。特别是这些铱碘桥聚合物能与含氮配体发生sp2C-H键活化反应,制备了一系列环金属化的双核铱化合物。而且,我们发现这些铱碘桥聚合物和衍生的膦配位双核铱化合物是胺的交叉偶联反应良好的催化剂。
报导了多个茚基膦配体与Ru3(CO)12的反应,分离并鉴定了一系列三核和四核的钉簇合物。这些反应的发生通过了C-H键和C-P键断裂,茚环上甲基取代基的位置强烈影响了C-H键和C-P键断裂的模式。我们还分离到一个通过分子内甲基sp3C-H键的活化的产物,这是一例稀有的磷原子协助的钉簇合物活化sp3C-H键的反应。
In this dissertation, the stoichiometric and catalytic C-H bond activation reactions of several series of cyclopentadienyl late-transition-metal complexes were studied. They are helpful for us to further understand the mechanism of C-H bond activation and promote their applications in organic synthesis.
A highly efficient rhodium-catalyzed cascade oxidative annulation leading to naphtho[1,8-bc]pyran derivatives has been developed. These reactions proceeded by sequential cleavage of C(sp2)-H/C(sp3)-H and C(sp2)-H/O-H bonds. Moreover, these reactions are highly regioselective with unsymmetrical alkynes. The further experiments indicated that the cascade reaction is a stepwise process, wherein the1-naphthol acts as an intermediate. Most of the naphtho[1,8-bc]pyran products exhibit intense fluorescence in the solid state.
Photochemical C-H bond activation and subsequent aerobic oxidation reactions of benzene with (η5-C5Me5)Ir(CO)2afforded a mononuclear iridium complex, three dinuclear iridium complexes, and a novel hexanuclear iridium cluster. The reactivities of some obtained iridium complexes were studied and their formation mechanisms were analyzed.
Iodo-bridged polymeric iridium complexes{(C5Me4)(CH2)n(C5Me4)(IrI2)2}m (n=2-4) were synthesized and used as the starting material to synthesize a series of dinuclear iridium complexes. Specially, the reactions of these iodo-bridged polymeric iridium complexes with several nitrogen ligands afforded cyclometallated dinuclear iridium complexes via C(sp2)-H bond activation. Moreover, these iodo-bridged polymeric iridium complexes and derivative phosphine-coordinated dinuclear iridium complexes could serve as efficient catalysts in the selective amine cross-coupling reaction.
The reactions of a series of indenylphosphines derivatives with Ru3(CO)12were studied and trinuclear and tetranuclear clusters were obtained via C-H bond and C-P bond activation. The position of methyl substituents on the indenyl ring strongly affects the mode of C-H and C-P bond activation. Moreover, an intramolecular C(sp3)-H bond activated product was isolated, which represents a rare example of C(sp3)-H bond activation by ruthenium clusters with assistance from coordinated phosphorus atom.
发展了一类茂铑化合物催化的串联氧化环化反应,能高效地合成萘并[1,8-bc]吡喃衍生物。该反应的发生经过了连续的sp2C-H键/sp3C-H键和sp2C-H键/O-H键的断裂,而且两步与不对称炔烃的环化反应都具有高度区域选择性。进一步实验表明炔烃插入是一个分步的过程,而1-萘酚衍生物是一个中间体。得到的大部分萘并[1,8-bc]吡喃产物都展示出了较强的固态荧光性质。
研究了(η5-C5Me5)Ir(CO)2苯溶液的光照C-H键活化以及随后在空气中的氧化反应,得到了一个单核铱化合物、三个双核铱化合物和一个结构新颖的六核铱簇合物,而且我们进一步研究了所得部分化合物的反应性和相互转换关系,并对这些化合物形成机理做了进一步分析。
制备了一系列桥连茂型铱碘桥聚合物{(C5Me4)(CH2)n(C5Me4)(IrI2)2},m (n=2-4),并以它们为起始原料合成了一系列双核铱化合物。特别是这些铱碘桥聚合物能与含氮配体发生sp2C-H键活化反应,制备了一系列环金属化的双核铱化合物。而且,我们发现这些铱碘桥聚合物和衍生的膦配位双核铱化合物是胺的交叉偶联反应良好的催化剂。
报导了多个茚基膦配体与Ru3(CO)12的反应,分离并鉴定了一系列三核和四核的钉簇合物。这些反应的发生通过了C-H键和C-P键断裂,茚环上甲基取代基的位置强烈影响了C-H键和C-P键断裂的模式。我们还分离到一个通过分子内甲基sp3C-H键的活化的产物,这是一例稀有的磷原子协助的钉簇合物活化sp3C-H键的反应。
In this dissertation, the stoichiometric and catalytic C-H bond activation reactions of several series of cyclopentadienyl late-transition-metal complexes were studied. They are helpful for us to further understand the mechanism of C-H bond activation and promote their applications in organic synthesis.
A highly efficient rhodium-catalyzed cascade oxidative annulation leading to naphtho[1,8-bc]pyran derivatives has been developed. These reactions proceeded by sequential cleavage of C(sp2)-H/C(sp3)-H and C(sp2)-H/O-H bonds. Moreover, these reactions are highly regioselective with unsymmetrical alkynes. The further experiments indicated that the cascade reaction is a stepwise process, wherein the1-naphthol acts as an intermediate. Most of the naphtho[1,8-bc]pyran products exhibit intense fluorescence in the solid state.
Photochemical C-H bond activation and subsequent aerobic oxidation reactions of benzene with (η5-C5Me5)Ir(CO)2afforded a mononuclear iridium complex, three dinuclear iridium complexes, and a novel hexanuclear iridium cluster. The reactivities of some obtained iridium complexes were studied and their formation mechanisms were analyzed.
Iodo-bridged polymeric iridium complexes{(C5Me4)(CH2)n(C5Me4)(IrI2)2}m (n=2-4) were synthesized and used as the starting material to synthesize a series of dinuclear iridium complexes. Specially, the reactions of these iodo-bridged polymeric iridium complexes with several nitrogen ligands afforded cyclometallated dinuclear iridium complexes via C(sp2)-H bond activation. Moreover, these iodo-bridged polymeric iridium complexes and derivative phosphine-coordinated dinuclear iridium complexes could serve as efficient catalysts in the selective amine cross-coupling reaction.
The reactions of a series of indenylphosphines derivatives with Ru3(CO)12were studied and trinuclear and tetranuclear clusters were obtained via C-H bond and C-P bond activation. The position of methyl substituents on the indenyl ring strongly affects the mode of C-H and C-P bond activation. Moreover, an intramolecular C(sp3)-H bond activated product was isolated, which represents a rare example of C(sp3)-H bond activation by ruthenium clusters with assistance from coordinated phosphorus atom.
引文
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