Catalytic Addition of be-ta-C-H Bond in Aliphatic Carbonyl Derivatives to Unsaturated Bonds

2018 Fiscal Year Final Research Report

• Project/Area Number: 16K21441
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry; Organic chemistry
• Research Institution: Tokyo University of Technology
• Principal Investigator: UENO Satoshi 東京工科大学, 工学部, 講師 (50514139)
• Project Period (FY): 2016-04-01 – 2019-03-31
• Keywords: 炭素-炭素結合形成 / 炭素-水素結合官能基化 / カルボニル化合物 / 4-クロモン / 4-キノロン

Outline of Final Research Achievements

The carbon-carbon bond is the fundamental framework of organic molecules, and the development of innovative methods for the C-C bond formation is important. The reaction with 100% atomic efficiency to selectively convert one of many carbon-hydrogen bonds to a carbon-carbon bond is limited to a type of reaction in which a carbon-hydrogen bond is added to an unsaturated bond. In this project, we have found selective addition of the be-ta-C-H bond of the carbonyl compound to obtain the desired product with low yield. Furthermore, in the course of this project, a novel synthetic method of 4-quinolone and 4-chromone was found through a new molecular transformation of be-ta-C-H bond and unsaturated bond.

Free Research Field

有機合成化学、有機金属化学

Academic Significance and Societal Importance of the Research Achievements

有機化合物は、医薬品や農薬、有機材料など多くの場面でわれわれの日常生活に役立っている。しかし現状ではそれらの有機化合物を合成するためには多くの廃棄物が生じる。今回、副生成物を一切生じないいわゆる原子効率100%で有機化合物を合成する方法の開発を行ない、低収率ながら目的生成物を得ることができた。今後引き続き研究を行なっていく。この手法が確立されれば有機合成化学に大きな進歩をもたらし、有機化合物のコスト削減や環境問題の緩和などの社会的な意義をもたらすと考えている。