open access

https://doi.org/10.14943/doctoral.k15637

https://hdl.handle.net/2115/90811

高酸化度化学種を利用した炭素-炭素不飽和結合の修飾

英語

2023-09-25

Hokkaido University

68p.

Carbon-Carbon (C-C) multiple bonds, serving as the cornerstone of many organic compounds extracted from petroleum resources and obtained from natural origins, act as key site for functional group attachment, thereby enabling the evolution of base molecules into value-added, complex chemical structures. This bond serves as a fertile platform for functional group introduction, facilitating the transformation of base molecules into more complex structures with considerably higher value. Carbon-Carbon multiple bonds exhibit inherent nucleophilic characteristics primarily due to their rich electron density. This unique property makes them particularly attractive in organic synthesis as they are amenable to modifications through a diverse array of reactions with electrophilic counterparts. The hydration reaction, carried out in acidic aqueous solutions such as sulfuric acid, stands as a classic example of the potential for multiple bond modification. Harnessing the reactivity of C-C multiple bonds for functionalization necessitates the creation of highly electrophilic active species. One prevalent strategy to achieve this involves the employment of high oxidation state chemical species. Such chemical species are inherently electron-deficient due to their high oxidation state, thereby exhibiting enhanced electrophilicity. This characteristic makes them ideal for initiating reactions with electron-rich C-C multiple bonds. The use of high oxidation state chemical species, hence, presents a compelling route to the functionalization of C-C multiple bonds. I delve into this topic further by categorizing these reactions into two primary types: those catalyzed by transition metals and those involving nonmetallic chemical species. In the sections that follow, these reactions will be analyzed, aiming to uncover the full potential of C-C multiple bond modification reactions using high oxidation state chemical species.

2023-09-25

甲第15637号

博士(理学)

(主査) 教授 永木 愛一郎, 教授 澤村 正也, 教授 伊藤 肇, 准教授 清水 洋平

総合化学院（総合化学専攻）

博士論文

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