Development of Molecular Transformations by Means of Light and Metals Directing towards Straightforward Synthesis

2019 Fiscal Year Final Research Report

• Project/Area Number: 15H05756
• Research Category: Grant-in-Aid for Scientific Research (S)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Kyoto University
• Principal Investigator: Murakami Masahiro 京都大学, 工学研究科, 教授 (20174279)
• Co-Investigator(Kenkyū-buntansha): 三浦 智也 京都大学, 工学研究科, 准教授 (10378804) ; 増田 侑亮 京都大学, 工学研究科, 特定助教 (20822307) ; 石田 直樹 京都大学, 工学研究科, 講師 (70512755) ; 矢田 陽 京都大学, 工学研究科, 助教 (70619965)
• Project Period (FY): 2015-05-29 – 2020-03-31
• Keywords: 分子変換 / 光 / 触媒

Outline of Final Research Achievements

Synthetic transformations of readily available materials such as hydrocarbons were developed by exploiting light and metal catalysts, providing a straightforward access to valued structural motifs. For example, a C-H bond of simple hydrocarbons was cleaved and CO2 was inserted therein to furnish carboxylic acids. Even saturated hydrocarbons, which are generally unreactive, could be used as the substrates. Also developed were stereoselective synthetic pathways from terminal alkynes to homoallylic alcohols with contiguous stereocenters. The process involves (1) introduction of boron groups onto alkynes to prepare alkenylboranes, (2) transposition of the alkene moiety of the alkenylboranes to generate allylboranes, (3) allylation of aldehydes with the generated allylboranes. A variety of homoallylic alcohols were synthesized in an enantio- and diastereo-selective fashion.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

有機合成化学には、医薬品や高機能材料に至るまで、社会が必要とする様々な有機化合物を合成するためのより良い手法を提供することが求められている。本研究で開発した直截的な合成法は、合成プロセスの効率化、ひいては医薬品や高機能材料の開発に資すると考えられる。