FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[C:12](=[O:17])[CH2:11][CH2:10]2)(=O)=O.[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[F-].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[CH3:16])[C:12](=[O:17])[CH2:11][CH2:10]3)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1A solution of 5-(trifluoromethanesulfonyloxy)-6-methyl-1-indanone 0.15 g, 0.51 mmol, from Step A), 4-benzyloxyphenyl boronic acid (0.17 g, 0.77 mmol), palladium acetate (5.7 mg, 0.025 mmol), tricyclohexylphosphine (8.6 mg, 0.030 mmol) and potassium fluoride (0.098 g, 1.68 mmol) in tetrahydrofuran (2.5 mL) was stirred at rt. After 5 min, the reaction was loaded onto silica gel and the product eluted with 25% ethyl acetate/hexanes to give a yellow solid (0.20 g): ESI-MS 329.1 (M+H).
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