[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10](C([Sn])=C(CCCC)CCCC)[CH2:11]CC.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:8]=[C:7]([CH:10]=[CH2:11])[CH:6]=[CH:5][C:3]=1[NH2:4]
A solution of 2-fluoro-4-iodoaniline (2.37 g, 10 mmol) in toluene (50 mL) was treated with tetrakis(triphenylphosphine)palladium (0.578 g, 0.5 mmol), tributylvinyltin (3.5 mL, 12 mmol) and a catalytic amount of 2,6-di-tert-butyl-4-methylphenol. After being heated at 100° C. for 1 h, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:5) as eluant to afford 2-Fluoro-4-vinylaniline (20-1, LJO-324, 1.275 g, 93%) as a yellow oil.
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