Bv. Nguyen et Dj. Burton, A NEW ROUTE FOR THE PREPARATION OF SUBSTITUTED 2,2-DIFLUOROSTYRENES AND A CONVENIENT ROUTE TO SUBSTITUTED (2,2,2-TRIFLUOROETHYL)BENZENES, Journal of organic chemistry, 62(22), 1997, pp. 7758-7764
The (2,2-difluoroethenyl)zinc reagent II is coupled with aryl iodides
or bromides in the presence of Pd(PPh3)(4) in DMF to give the correspo
nding 2,2-difluorostyrenes IV. The 4-substituted (tetrafluoroaryl)copp
er reagents are coupled with 2,2-difluoro-1-iodoethylene (I) to produc
e the corresponding styrene derivatives VII. Both methods provide good
yields of the coupled products. These products react with wet KF in D
MF or DMSO to form the (2,2,2-trifluoroethyl)benzene derivatives VIII
in good yields.