1993 Fiscal Year Final Research Report Summary

Active Fluoro-intermediate for Fluorinated Heterocycles

Research Project

Project/Area Number	04453101
Research Category	Grant-in-Aid for General Scientific Research (B)
Allocation Type	Single-year Grants
Research Field	Synthetic chemistry
Research Institution	Okayama University
Principal Investigator	UNEYAMA Kenji Department of Applied Chemistry, Professor, 工学部, 教授 (00033150)
Co-Investigator(Kenkyū-buntansha)	SAKAI Takashi Department of Applied Chemistry, Associate Professor, 工学部, 助教授 (00170556)
Project Period (FY)	1992 – 1993
Keywords	Fluoro-compound / Fluorination / Electrolysis / フッ素化合物
Research Abstract	Trifluoroacetimidoyl metals (Li, Zn, Pd) and telluride have been prepared as precursors for the trifluoroacetimidoyl carbanion and the corresponding radicals and have been employed for the synthesis of fluorinated nitrogen heterocycles. Photolysis of the telluride leads to homolytic cleavage of the C-Te bond to generate the desired trifluoroacetimidoyl radical which undergoes intramolecular cyclization. The reaction provided 3-oxy-2-trifluoro methyl indols (3). Meanwhile, palladium catalyzed carboalkoxylation of the trifluoroacetimidoyl iodides and subsequent alkylation and hydrogenation provided various kinds of fluorinated -aminoacids. Lithium-iodine exhange reaction of the iodides generated the acetimidoyl lithium which is stable below -65 C and alkylated. By these newly developed methods, some interesting heterocycles (2) - (4) have been synthesized.

(6 results)