C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].[F:16][C:17]1[N:22]=[C:21]([F:23])[C:20]([F:24])=[C:19](F)[C:18]=1[F:26].[F-].[Cs+].ClCCl>CN(C=O)C.[Cl-].[Na+].O>[F:23][C:21]1[C:20]([F:24])=[C:19]([C:3]#[C:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:11]([O-:13])=[O:12])[C:18]([F:26])=[C:17]([F:16])[N:22]=1
A solution of Trimethyl((2-nitrophenyl)ethynyl) silane, (11c) (1.10 g, 5.02 mmol) in DMF (10 mL) was added to the mixture of pentafluoropyridine (1.08 g, 6.53 mmol) and CsF(1.10 g, 7.52 mmol) in DMF (10 mL) slowly. The reaction mixture was stirred overnight. Brine (30 mL) and dichloromethane (60 mL) were added. Organic phase was separated and washed with water (30 mL×3). Solvent was evaporated by rotary evaporation and the residue was chromatographed (Hexane, then EtOAc:Hexane =1:30) to provide the desired product in 77% yield: 1H-NMR (300 MHz, CDCl3) δ 8.24 (dd, J=7.8, 1.5 Hz, 1H), 7.85 (dd, J=7.5, 1.5 Hz, 1H), 7.73 (ddd, J=7.5, 7.5, 1.5 Hz, 1H), 7.66 (ddd, J=7.8, 7.8, 1.5 Hz, 1H); 13C-NMR (150 MHz, CDCl3) δ 149.7, 143.7 (dm, J=234.1 Hz), 142.1 (dm, J=264.7 Hz), 135.5, 133.5, 131.2, 125.3, 116.7 (t, J=16.3 Hz), 116.2, 100.9 (t, J=3.2 Hz), 79.8 (t, J=4.1 Hz); HRMS (CI+): calcd for C13H5F4N2O2 [M+H]+ 297.02872, found 297.02911; m.p. 109-110° C.
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