Development of Reusable Organic Group Transfer Agent Based on Boron Art Complex

2020 Fiscal Year Final Research Report

• Project/Area Number: 18K05135
• 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: Kanazawa University (2019-2020); Institute of Physical and Chemical Research (2018)
• Principal Investigator: Sumida Yuto 金沢大学, 薬学系, 助教 (40630976)
• Project Period (FY): 2018-04-01 – 2021-03-31
• Keywords: ホウ素アート錯体 / 直接光励起 / アルキルラジカル

Outline of Final Research Achievements

In this study, we have found a boron-ate complex that can be stably handled available from the corresponding a strong nucleophile, such as organolithium or organoagnesium to the robust and highly planar pentacyclic boron compound boracene. The organic groups on the boron can be selectively used for the synthetic methodology. In particular, under visible light irradiation, the direct excitation and homolytic or mesolytic cleavage of carbon-boron bond occurs to the formation of alkyl radical derived from the organic group. This is an attractive method for the generation of carbon-centered radical generation triggered only by visible light, which provides a new approach to organic synthesis.

Free Research Field

有機合成化学　有機金属化学

Academic Significance and Societal Importance of the Research Achievements

本研究では，ホウ素原子が環状分子骨格に埋め込まれた「ボラセン」から調製される有機ホウ素アート錯体を独自に設計・合成した。有機ホウ素アート錯体と可視光により発生させた炭素ラジカルは，化学反応の炭素源として活用でき，これまで到達困難とされていた複雑かつかさ高い有機化合物などをつくり出せる。本研究成果は，有機ホウ素化合物と光エネルギーを組み合わせることで可能となる新しい有機合成技術を提供したといえ，創薬研究などをより一層加速させるものと期待される。