N-雜環卡賓（NHC）σ-捐贈作為強大的中性配廣泛用作輔助配體在協助調解催化過渡金屬。我們成功地採用了氨基聯NHC的（1-TBU）調解與各種芳基碘苯和吡啶，不涉及過渡金屬的交叉耦合。我們還發現了另一個系統，使用雙亞胺吡啶配體調解之間的苯和各種芳基碘芳基。已配體的特點是多核（1H，13C）核磁共振光譜，其中一些已經由單晶X-射線衍射特徵。交叉偶聯反應產生的化合物也已被鑑定多核核磁共振，核磁共振光譜和質譜測量。
此外，我們還調查1 TBU系統的動力學同位素效應和激進的途徑。我們發現，金屬碳 - 碳耦合通過單電子轉移機制與自由基中間體多方面參與。我們的發現表明，1 TBU和雙亞胺吡啶配體有前途的交叉耦合，而不訴諸使用過渡金屬調解活動。

N-Heterocyclic Carbene (NHC) as strong neutral σ-donating ligands are widely utilized as auxiliary ligands in assisting transition metal for mediating catalysis. We successfully employed Amino-Linked NHC (1-tBu) to mediate cross coupling of benzene and pyridine with various aryl iodide without involving transition metal. We also found another system using Bis Imino Pyridine as a ligand to mediate arylation between benzene and various aryl iodide. The ligands have been characterized by multinuclear (1H,13C) NMR spectroscopy and some of them have been characterized by single-crystal X-ray diffraction. All of compounds produced from cross coupling reaction also have been characterized by multinuclear 1H NMR, 13C NMR spectroscopy and MS measurements.
In addition, we also investigate kinetic isotope effect and radical pathway in 1-tBu system. We found that the metal-free carbon-carbon coupling manifold via single electron transfer mechanism with radical intermediates involved. Our finding has demonstrated that 1-tBu and Bis Imino Pyridine as a ligand have promising activity for mediating cross coupling without resorting to use transition metal.

Acknowladgement
Abstract
Chapter 1 Introduction
1.1 Carbene
1.2 Nitrogen-Heterocyclic Carbene (NHCs)
1.3 The NHC’s Application in Organometallic Chemistry and Catalysis
1.4 Metal-Free Catalyst System in Organocatalyst for Arylation Reaction
Chapter 2 Result and Discussion
2.1 Synthesis and Characterization of Amino-Linked Carbene
2.2 Synthesis and Characterization of Bis Imino Pyridine
2.3 Amino-Linked Carbene Catalyzed Arylation of Benzene
2.4 Bis Imino Pyridine Catalyzed Arylation of Benzene
Chapter 3 Experimental
3.1 General Procedure....
3.2 Material and Methods
3.3 General Procedure for Cross-Coupling of Aryl Iodides with Benzene
3.4 General Procedure for Cross-coupling of Aryl Iodides with Pyridine
3.5 General Procedure for Arylation of Benzene with Aryl Iodide in the Presence of Bis Imino Pyridine
3.6 The synthesis of Ligand
3.7 Study Kinetic Isotope Effect
3.8 Competition Reaction Between Benzene and Pyridine
Chapter 4 Conclusion
Chapter 5 Reference
Appendix A : Single Crystal X-ray Characterization
Appendix B : 1H and 13C NMR Spectra

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