Abstract
Copper(II) acetylacetonate immobilized in ionic liquids efficiently catalyzes aziridination of olefins in good yields at a faster rate than the earlier reported methods using PhI=NTs as a nitrene donor with easy catalyst/solvent recycling.
Key words
copper acetylacetonate - ionic liquids - aziridination - olefins - PhI=NTs
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Typical Experimental Procedure : Cu(acac)2 (0.010 g, 7.7 mol%), styrene (0.56 ml, 5 mmol) and PhI=NTs (0.372 g, 1 mmol) were added to the ionic liquid (1 mL) and the reaction mixture was stirred at r.t. for 25 min. The reaction was monitored by the disappearance of PhI=NTs. After completion of the reaction, the product was extracted with Et2 O (3 × 4 mL) by simple decantation and purified by column chromatography on silica gel with petroleum ether and EtOAc (95:5) as eluent. The ionic liquid containing Cu(acac)2 was dried under vacuum for the next run. The resulting products were analyzed by NMR. Yield: 0.240 g, 88%. 1 H NMR (400 MHz, CDCl3 ): δ = 7.86 (d, J = 8.3 Hz, 2 H, Ar-H), 7.27 (m, 7 H, Ar-H), 3.77 (dd, J
cis
= 7.2 Hz, J
trans
= 4.5 Hz, 1 H, CHPh), 2.98 (d, J = 7.8 Hz, 1 H, cis- CH-aziridine) 2.43 (s, 3 H, Ar-Me), 2.38 (d, J = 4.4 Hz, 1 H, trans -CH-aziridine).
