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Synthesis of novel heterocyclic carbenes and their transition metal compounds , characterization and catalytic performance testing

Author: ZhongZuo
Tutor: HouXiuFeng
School: Fudan University
Course: Inorganic Chemistry
Keywords: N-heterocyclic carbenes multifunctional catalysts counterions heterometallic transition metal catalyzed
CLC: O627
Type: Master's thesis
Year: 2011
Downloads: 181
Quote: 0
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Abstract


N-Heterocyclic carbenes (NHCs), ubiquitous ligands for homogeneous catalysts, can bind to a wide range of metals with different oxidation states, affording transition metal compounds that are generally resistant to decomposition. The N-heterocyclic carbene system is now regarded as a prospective replacement catalyst for phosphane ligands. Since Herrmann et al. prepared the first catalysts based on NHCs ligands, many researchers have focused their efforts on the design of novel NHCs ligands and complexes that can compete with or show superior catalytic reactivity over their phosphane analogues. In view of the broad prospect of N-Heterocyclic carbenes, this thesis describes the synthesis and catalytic study of NHCs and their metal complexes as follows:In section one:A class of salicylaldiminato imidazolium salt with both Schiff base and imidazolium salt moiety was used to synthesize heterometallic compounds, which could serve as multifunctional catalysts in designed tandem processes. The successful preparation of seven single-nuclear compounds with a series of transition metals (Pd, Ir, Ru, Zn, Ni) illustrated the high versatility of this class of ligands, which is crucial for the design of catalysts. Synthesis of homo-dinuclear compounds and hetero-trinuclear compounds provided practical methods to connect multiple metal fragments through these ligands. The heterometallic complex (Ir/Ni) was employed as a catalyst in a designed tandem reaction of dehalogenation/transfer hydrogenation of halo-acetophenones. This preliminary catalytic study showed that the heterometallic species is more active than combination of the corresponding single-metallic species.In section two:Seven tripodal imidazolium salts were synthesized and used as catalyst precursors in cross-coupling reactions of aryl halides with arylboronic acids. Effect of counterions and central cores of seven tripodal imidazolium salts was investigated. The tripodal imidazolium salt anchored to benzene with anion PF6- was found most effective with Pd(OAc)2 for the cross-coupling of aryl bromides with arylboronic acids.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds
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