Vinylic C-F bond activation with low-valent zirconocene: the generation and cross-coupling reactions of 1-fluorovinylzirconocene

(p-2,2-Difluorovinyloxyphenyl)dimethylamine, readily obtained from 2,2,2-tr ifluoroethanol, is treated with zirconocene equivalent 'Cp2Zr' to generate thermostable 1-fluorovinylzirconocene via a C-F bond cleavage. This 1-fluor ovinylzirconocene can be used for C-C bond formation through the cross-coup ling with aryl iodides in the presence of palladium catalyst and zinc iodid e, leading to (Z)-1-aryl-2-(p-dimethylaminophenoxy)-1-fluoroolrfins in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.