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2021 Fiscal Year Final Research Report

Development of Novel Direct Functionalization Methodology of 1,2-Azaborines

Research Project

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Project/Area Number 20K22522
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeMulti-year Fund
Review Section 0501:Physical chemistry, functional solid state chemistry, organic chemistry, polymers, organic materials, biomolecular chemistry, and related fields
Research InstitutionTokyo Institute of Technology

Principal Investigator

Morita Taiki  東京工業大学, 科学技術創成研究院, 助教 (80881929)

Project Period (FY) 2020-09-11 – 2022-03-31
Keywordsアザボリン / 不斉合成 / 直接官能基化 / BN複素環化合物 / パラジウム触媒
Outline of Final Research Achievements

The BN heterocycles which contain boron and nitrogen atoms in their ring systems have attracted immense interest in various research fields represented by organic luminescent materials. In addition, recent studies revealed their great potential as bioactive molecules. These widespread application of BN heterocycles have invoked the development of novel synthetic methodologies for highly functionalized BN heterocycles. In this work, we focused on the direct functionalization of 1,2-azaborines, and succeeded in palladium-catalyzed N-H/B-H double functionalization of them via cycloaddition with vinylethylene carbonate. Furthermore, we achieved the asymmetric cycloaddition by employing a chiral ligand, which is the first example of enantioselective direct functionalization of 1,2-azaborines.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究によって得られる光学活性な多環性BN複素環化合物は、既存の合成手法では合成困難である。とくに、これまでキラルなBN複素環化合物の合成例はほとんどなかったことから、本研究で初めて達成された1,2-アザボリン類の直接的不斉官能基化は学術的に意義深い。また、開発した官能基化手法をもとに、環のサイズや置換様式の異なる様々なBN複素環化合物の創出も期待できることから、本研究はBN複素環化合物を基軸とした新規医農薬品の創製に大きく貢献できる。

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Published: 2023-01-30  

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