Challenging Study on Difluoromethylation of Boron directed toward BNCT Drugs

2016 Fiscal Year Final Research Report

• Project/Area Number: 26620078
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: Mikami Koichi 東京工業大学, 物質理工学院, 教授 (10157448)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: フッ素化学 / ホウ素化合物 / リチウム

Outline of Final Research Achievements

Hitherto unknown difluoromethylated (CF2H) boron derivatives should be employed as a brand-new BNCT (boron neutron capture therapy)drugs. The CF2H moiety has been recognized as one of the lipophilic bioisostere of hydroxy group. The CF2H-B derivatives are thus expected to be the key in the development of novel biofunctional compounds such as L-amino acids-based difluoromethylboron congener for BNCT.
We have already developed the Umpolung approach of fluoroform (HCF3, HFC-23) for the synthesis of difluoromethyl-substituted compounds. The C-F bond in CF3H can be activated and hence substituted by appropriate organolithium nucleophiles. Therefore, nucleophilic boryllithium is promising to synthesize the desired air-stable difluoromethylated boron compounds via the C-F activation. We herein demonstrate the C-F activation of fluoroform by boryllithium. Structural characterization of the difluoromethylated boron compounds was also carried out.

Free Research Field

有機フッ素化学