Convenient protocols for Mizoroki-Heck reactions of aromatic bromides and polybromides with fluorous alkenes of the formula H 2 C[double bond, length as m-dash]CH(CF 2 ) n-1 CF 3 (n = 8, 10).

The fluorous alkenes H ₂ C[double bond, length as m-dash]CHR _fn (R _fn = (CF ₂ ) _n-1 CF ₃ ; n = 8, 10) undergo the Mizoroki-Heck reaction with a variety of aromatic monobromides and polybromides such as 1,3- and 1,4-C ₆ H ₄ Br ₂ , 1,3,5-C ₆ H ₃ Br ₃ , 1,3,5-C ₆ H ₃ Br ₂ Cl, 1,4-XC ₆ H ₄ Br (X = CF ₃ , R _f8 , COCH ₃ , CN, 1,4-OC ₆ H ₄ Br), 1,2-O ₂ NC ₆ H ₄ Br, 5-bromoisoquinoline, 5-bromopyrimidine, 3-bromo-5-methoxypyridine, and 3,5-dibromopyridine (sixteen examples, 78% average isolated yield). Typically, 1.2-2.4 equiv. of alkene are employed per Ar-Br bond, together with Pd(OAc) ₂ catalyst (4-5 mol%/Ar-Br bond), n-Bu ₄ N ⁺ Br ^- (0.8-1.0 equiv./Ar-Br bond), NaOAc (1.2-2.4 equiv./Ar-Br bond), and 3 : 1 w/w DMF/THF as solvent (120 °C). No effort is necessary to exclude air or moisture, and reactions may be conducted on >10 g scales. Only E isomers of the products Ar(CH[double bond, length as m-dash]CHR _fn ) _m are detected. Thirteen representative examples are hydrogenated (Pd/C, balloon pressure H ₂ ), giving Ar(CH ₂ CH ₂ R _fn ) _m (92% average isolated yield).