1,10-Phenanthroline → 1-tert-Butoxycarbonyl-1-(4-phenylphenyl)hydrazine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

An oven-dried resealable Schlenk tube was charged with CuI (50 mg, 0.263 mmol, 5.1 mol %), 1,10-phenanthroline (100 mg, 0.555 mmol, 11 mol %), 4-iodobiphenyl (1.45 g, 5.18 mmol), Cs2CO3 (2.30 g, 7.06 mmol), evacuated and backfilled with argon. tert-Butyl carbazate (825 mg, 6.24 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 23 h. The resulting suspension was cooled to room temperature and filtered through a 1×1 cm pad of silica gel eluting with 50 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 4:1; 20 mL fractions). Fractions 9-20 provided 1.29 g (88% yield) of the product as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.64-7.59 (m, 2H), 7.57 (s, 4H), 7.48-7.43 (m, 2H), 7.38-7.33 (m, 1H), 4.50 (s, 2H), 1.56 (s, 9H).

Herkunft & Nachweise