Electrophilic Metalation of Alkenes Using Dissociation Equilibrium Property of Strong Lewis Acid and Weak Base

2019 Fiscal Year Final Research Report

• Project/Area Number: 17K14443
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Tohoku University
• Principal Investigator: Tanaka Shinya 東北大学, 環境保全センター, 講師 (80570142)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Keywords: Lewis酸 / 塩基 / アルケン / 求電子置換反応

Outline of Final Research Achievements

We investigated the development of substitution reaction of vinyl C-H bond of alkenes by utilizing the property that strong Lewis acid and weak base having suitable bulkiness are in dissociation equilibrium. As a result, we achieved electrophilic borylation and Friedel-Crafts acylation of alkenes. We also expanded the applicability of the carboxylation to substrates having coordinating functional groups by the choice of the combination of Lewis acid/base and substrate designing. Furthermore, we could obtain the promising knowledge about Friedel-Crafts alkylation and catalytic Friedel-Crafts acylation.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

アルケンの求電子置換反応は，プロトン脱離がとくに容易な場合を除いて進行しない．これに対して本研究は，適度なかさ高さの弱塩基を用いることでアルケン類の求電子的アルミニウム化やホウ素化を実現し，また，系内で発生させた求電子活性種をも塩基により失活させることなく求電子置換反応に利用できることも示した．これは，“アルケン類の求電子置換反応”を広く一般的化する方法論となるものであり，基礎化学的な意義が大きい．