Iron-Catalyzed Synthesis of Fused Aromatic Compounds via C–H Bond Activation (Springer Theses)

Iron Catalysts In Organic Synthesis Are Strongly In Demand Because Iron Is Non-toxic, Inexpensive, And The Most Abundant Transition Metal In The Earth, Although Their Use Is Still Limited Compared With That Of Rare, Precious Metals Such As Palladium, Ruthenium, And Rhodium. This Thesis Describes The First Practical Example Of Iron Catalysis In The Carbon–hydrogen Bond Activation Reaction To Synthesized Fused Aromatic Ring Compounds. By Using A Unique Combination Of Iron Catalyst And Dichloride Oxidant, Various Kind Of Naphthalene And Phenanthrene Derivatives Were Synthesized Via Annulation Reaction With Alkynes Including Direct C–h Bond Activation Process. This Achievement Opens The New Possibility Of Low-valent Iron Catalysis And Expands Synthetic Methods For A Sustainable Society. General Introduction -- Iron-catalyzed Naphthalene Synthesis From Alkyne And Grignard Reagent -- Iron-catalyzed Phenanthrene Synthesis From Alkyne And Grignard Reagent -- Iron-catalyzed Phenanthrene Synthesis From Alkyne And Aryl Bromide Mediated By Metallic Magnesium -- Summary And Perspectives. By Arimasa Matsumoto. Iron catalysts in organic synthesis are strongly in demand because iron is non-toxic, inexpensive, and the most abundant transition metal in the earth, although their use is still limited compared with that of rare, precious metals such as palladium, ruthenium, and rhodium. This thesis describes the first practical example of iron catalysis in the carbon ́ hydrogen bond activation reaction to synthesized fused aromatic ring compounds. By using a unique combination of iron catalyst and dichloride oxidant, various kind of naphthalene and phenanthrene derivatives were synthesized via annulation reaction with alkynes including direct C ́ H bond activation process. This achievement opens the new possibility of low-valent iron catalysis and expands synthetic methods for a sustainable society Front Matter....Pages i-xiii General Introduction....Pages 1-9 Iron-Catalyzed Naphthalene Synthesis from Alkyne and Grignard Reagent....Pages 11-22 Iron-Catalyzed Phenanthrene Synthesis from Alkyne and Grignard Reagent....Pages 23-64 Iron-Catalyzed Phenanthrene Synthesis from Alkyne and Aryl Bromide Mediated by Metallic Magnesium....Pages 65-71 Summary and Perspectives....Pages 73-74