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2018 Fiscal Year Final Research Report

Implementation of a new strategy in transition metal catalyzed functionalization of the sp3 carbon-hydrogen bond of carbonyl and amine compounds

Research Project

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Project/Area Number 16K05773
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionNational Institute of Advanced Industrial Science and Technology

Principal Investigator

Yada Akira  国立研究開発法人産業技術総合研究所, 材料・化学領域, 研究員 (70619965)

Project Period (FY) 2016-04-01 – 2019-03-31
Keywords炭素ー水素結合活性化 / 遷移金属触媒 / 窒素ー酸素結合切断
Outline of Final Research Achievements

In this research project, transition metal catalyzed sp3-carbon-hydrogen bond functionalization of carbonyl compounds and amine compounds, which are otherwise difficult to activate and functionalize previously, is studied in order to improve the practicality and efficiency of the C-H bond functionalization reaction. As the result, palladium-catalyzed carbon monoxide insertion reaction into the C-H bond at the β-position of N-carboxyl amine to furnish β-lactam is found. The reaction undergoes through the cleavages of nitrogen-oxygen and carbon-hydrogen bond in the molecule, which is scientifically interesting and mechanistically unprecedent.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究で得られた成果は、1つの分子内で窒素-酸素結合と炭素-水素結合の2種類の結合の切断を伴うというこれまでにほとんど知られていない形式で進行するものであり、学術的に極めて興味深いものである。また、標的分子の合成する工程を短縮できたり副生成物を最小限に抑えることもできるため、環境調和に優れた次世代型プロセスとして期待できる。さらに研究を進展させることによって、汎用性が高い炭素-水素結合の直接活性化・官能基化反応の開発につながることが期待される。

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Published: 2020-03-30  

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