Development of Building Blocks Using Selective Hydrometalation of Boronated Polyenes

2022 Fiscal Year Final Research Report

• Project/Area Number: 20K05489
• 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: Tokyo University of Agriculture and Technology
• Principal Investigator: Komine Nobuyuki 東京農工大学, 工学(系)研究科(研究院), 助教 (90302918)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: 1-ボリル-1-シリル-2,4-ジエン / ヒドロシリル化 / トリエニルボラン / クロスカップリング反応

Outline of Final Research Achievements

In this study, a novel catalytic synthesis of borylsilyldiene compounds via the hydrosilation of trienes containing a boryl group was established. Hydrosilylation of 1,3-butadienyl boronic esters catalyzed by a monophosphine palladium(0) complex proceeds to give 1-silyl-1-boryl-2-butene derivatives. Similarly, 1-boryl-1-silyl-2,4-pentadiene derivatives were synthesized by the hydrosilylation of 1,3,5-hexatrienyl boronic esters with HSiPh3 in the presence of a monophosphine palladium(0) catalyst with alkylphosphines such as PMe3 and PBu3. In contrast, the (mono)triphenylphosphine palladium(0) complex mainly produced 1-boryl-3-silyl-1,4-pentadiene derivatives.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究ではホウ素置換基を有するトリエン誘導体のヒドロシリル化による1,1-二置換型シリルボリル化合物の効率的な合成法を確立した。また、その過程で1,3-二置換型シリルボリル化合物の効率的な合成にも成功した。これらの化合物のボリル基とシリル基間の反応性の違いを利用した複数の結合生成を連続的かつ選択的に行うことで、ジエン骨格を有する有用化合物の合成への応用が期待される。