Development of Direct Arylation Reaction of Aliphatic C-H Bonds through a Radical Chain Mechanism

2021 Fiscal Year Final Research Report

• Project/Area Number: 19H02728
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Kwansei Gakuin University
• Principal Investigator: Shirakawa Eiji 関西学院大学, 生命環境学部, 教授 (70273472)
• Project Period (FY): 2019-04-01 – 2022-03-31
• Keywords: ラジカル反応

Outline of Final Research Achievements

We have developed the direct C-H arylation of aliphatic compounds with aromatic compounds, utilizing homolytic aromatic substitution pathway consisting of addition of an aliphatic carbon radical and elimination of a heteroatom radical. Here alcohols, alkylamides, ethers and alkyl formates are arylated with sulfonylarenes or alkyl halides by treatment with a substoichiometric amount of a tert-butoxy radical precursor to give benzylic amines, N-benzylic amides, benzyl ethers and alkylarenes.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

α-ヘテロ原子置換アルキル基を芳香環に導入する反応の開発は，その生成物の有用性から有機合成上重要である．本研究で実現した反応は，遷移金属などの希少で有毒なものを用いることなく，また脂肪族化合物を予め修飾することなく C-H 結合をそのまま変換する反応であり，その汎用性から学術的にも社会的にも意義深いものと言える．