[Li+].[Cl-].[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11](OS(C(F)(F)F)(=O)=O)=[CH:12]2)=[CH:7][CH:6]=1.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:13](=[CH:12][C:11]([CH:23]=[CH2:24])=[CH:10][CH:9]=2)[CH:14]=1To a mixture of (Ph3P)2PdCl2 (1.752 g), LiCl (6.36 g), and trifluoromethanesulfonic acid 7-methoxy-naphthalen-2-yl ester (15.3 g) was added dropwise tributyl(vinyl)tin (19.02 g). The resulting mixture was stirred over 4 h at 90° C. The reaction was quenched with water and extracted with CH2Cl2. The organic layer was washed with water and dried over MgSO4. After concentration, the crude product was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to give the title compound as an oil (9 g).
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