Novel Bond Formation Reactions of Aromatic Compounds Using Heteroatom Activation

2023 Fiscal Year Final Research Report

• Project/Area Number: 20K05520
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Ritsumeikan University
• Principal Investigator: Morimoto Koji 立命館大学, 薬学部, 講師 (10543952)
• Project Period (FY): 2020-04-01 – 2024-03-31
• Keywords: 超原子価ヨウ素 / アミノ化 / グリコシル化

Outline of Final Research Achievements

In organic chemistry, cross-coupling reactions are important for the formation of various bonds such as carbon-carbon and carbon-nitrogen bonds, and are indispensable for the synthesis of pharmaceuticals, agrochemicals, and organic materials. In this study, we succeeded in the coupling reaction with phenothiazines as a C-N bond forming reaction. Furthermore, by reacting thioglycosides with hypervalent iodine reactants derived from carboxylic acids, we succeeded in synthesizing acyl-O-glycosyl compounds. These acyl-O-glycosyl compounds reacted with thioglycoside acceptors to form disaccharides, and the method was repeated to synthesize trisaccharides and tetrasaccharides by a simple procedure.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

一般的に酸化的手法はハロゲン化やメタル化といった官能基化が予め必要な遷移金属を用いた結合形成反応に比べ、原料の構造修飾を必要としない直接的かつ簡便で、副産物の少ない手法である。しかし官能基変換を必要としない方法は慨して選択的が低いことが問題である。今回開発した手法は、重金属酸化剤よりも緩和な酸化能を有する3価の超原子価ヨウ素反応剤を用いるため、環境調和型の結合形成反応としてより優れた手法である。