Cross-coupling reactions aziridine

The catalyst system mentioned above does not work for aliphatic aziridines. However, after changing the iV-sulfonyl group from tosyl to cinsyl (32) the cross-coupling reaction of aliphatic aziridines can be carried out by NiCla glyme catalysis (Scheme 14.39). In this case carbon-carbon bond formation on the least-substituted side of the aziridine is favoured, the ratios of the regioisomers being from 2.5 1 to 4.9 1. ° ... 

Munegumi T, Azumaya I, Kato T et al (2006) [3 + 2] Cross-coupling reactions of aziridines with isocyanates catalyzed by nickel(II) iodide. Org Lett 8 379-382... 

The reactivity of A-heterocyclic carbenes (NHC) with iron has been presented through the various types of complexes that have been described. Their catalytic applications in cross-coupling, allylation, aziridination, hydrosilylation, and as hydrogenase mimics are detailed. A report on cross-coupling reactions catalysed by complexes of iron group metals with NHC features the reaction mechanisms. ... 

More recently, Takeda et reported [Pd(SlPr)(cin)Cl)] (39) to be highly efficient in the regioselechve and stereospecific cross-coupling of enantiopure 2-arylaziridines with arylboronic acids. Using 4 mol% of the pre-catalyst, a variety of chiral 2-aryl-phenethylamine derivatives were produced under mild reaction conditions in high yield and with excellent enantioselectivity (up to 99% ee, Scheme 17). Electron neutral and electron deficient aziridines and sterically encumbered and/or funchonalized aryl boronic acids were all well tolerated under the developed conditions. 

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