The nickel-catalyzed reduction of secondary and tertiary amides to give amine products is reported. The transformation is tolerant of extensive variation with respect to the amide substrate, proceeds in the presence of esters and epimerizable stereocenters, and can be used to achieve the reduction of lactams. Moreover, this methodology provides a simple tactic for accessing medicinally relevant α-deuterated amines.
Various N-aryl-2-alkynylazetidines were very efficiently converted to pyrrolo[1,2-a]indoles with gold catalysts, especially the 2-biphenyl-dicyclohexylphosphino-gold(I) hexafluoroantimonate, in dichloromethane at room temperature. Additionally, two formal syntheses of bioactive non-natural compounds, i.e. 7-methoxymitosene and an 5-HT(2C) receptor agonist, have been achieved.
Gold(I)-polyoxometalate hybrid complexes 1-4 ([PPh3AuMeCN]xH4-x SiW12O40, x=1-4) were synthesized and characterized. The structure of the primary gold(I)-polyoxometalate 1 (x=1) was fully ascertained by XRD, FTIR, (31)P and (29)Si magic-angle spinning (MAS) NMR, mass spectroscopy, and SEM-energy dispersive X-ray spectroscopy (EDX) techniques. Moreover, this complex exhibited better catalytic activity and selectivity compared with standard, homogeneous, gold catalysts in the new rearrangement of propargylic gem-diesters.
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