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Synthesis of Aziridines from Alkenes and Aryl Azides with a Reusable Macrocyclic Tetracarbene Iron Catalyst

2011; American Chemical Society; Volume: 133; Issue: 48 Linguagem: Inglês

10.1021/ja2090965

1943-2984

S. Alan Cramer, David M. Jenkins,

N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

A new iron aziridination catalyst supported by a macrocyclic tetracarbene ligand has been synthesized. The catalyst, [((Me,Et)TC(Ph))Fe(NCCH(3))(2)](PF(6))(2), was synthesized from the tetraimidazolium precursor ((Me,Et)TC(Ph))(I)(4) and characterized by NMR spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction. This iron complex catalyzes the aziridination of electron-donating aryl azides and a wide variety of substituted aliphatic alkenes, including tetrasubstituted ones, in a "C(2) + N(1)" addition reaction. Finally, the catalyst can be recovered and reused up to three additional times without significant reduction in yield.