[Cl-].[CH3:2][Si:3]([C:6]#[C:7][Zn+])([CH3:5])[CH3:4].[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15])([O-:11])=[O:10].[Cl-].[NH4+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](=[O:15])[C:7]#[C:6][Si:3]([CH3:5])([CH3:4])[CH3:2])([O-:11])=[O:10]The above solution of (trimethylsilyl)ethynyl)zinc(II) chloride (16) in THF was warmed to 0° C., and added to the mixture of 2-nitrobenzoyl chloride (0.94 g) and tetrakis(triphenylphosphine) palladium(0) (176 mg) in tetrahydrofuran at 0° C. under a N2 atmosphere. The reaction mixture was maintained at 0° C. for 30 minutes. Aqueous ammonium chloride solution was added to quench the reaction. It was then extracted 3-times with EtOAc (3×100 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by preparative TLC to give 300 mg of the desired product (11).
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