Functionalization of monofluoroallene and the synthesis of aryl-substituted conjugated fluorodienes.
[reaction: see text] 4-Fluoroallenol 3a, prepared from 1, cyclized easily to 4 but preserved its fluoroallenyl integrity under oxidation and S(N)2 displacement to yield aldehyde, amine, mesylate, and halide 6. Allylic isomerization yielded 2-halo-1-fluoro-1,3-butadiene 7, which underwent a Suzuki coupling to give aryl-substituted conjugated diene 8.
Lan
Yunfeng
Y
Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, Massachusetts 02747, USA.
Hammond
Gerald B
GB