Intermolecular Mono‐ and Dihydroamination of Activated Alkenes Using a Recoverable Gold Catalyst

Abstract

A combination of gold chloride organometallic complex and a silver salt was used to catalyze intermolecular hydroamination of activated alkenes, i.e aza‐Michael reactions. The gold‐catalyzed reactions of activated alkenes with nitrogen substrates were investigated and found to afford various mono‐ and dihydroamination products, the latter being rare and original. After flash chromatography, gold NHC catalyst could be recovered as a gold hydroxide NHC complex. When combined with a silver salt, the gold complex lead again to an active hydroamination catalyst.

Switching the Electron‐Donating Ability of Phosphines through Proton‐Responsive Imidazolin‐2‐ylidenamino Substituents

“…1,3‐Diisopropyl‐4,5‐dimethylimidazolin‐2‐imine (R 1 H), [AuCl(SMe 2 )], 2,6‐lutidinium triflate, 3 and 4 were prepared following literature procedures. All other compounds were purchased from commercial sources and used as received.…”

Chiral Phase‐Transfer‐Catalyzed Intramolecular aza‐Michael Reactions for the Asymmetric Synthesis of Isoindolinones

“…When R 2 was an O ‐alkyl group, the resulting isoindolinones 24a – c could be isolated in good yields, but poor enantiomeric excesses were obtained (Scheme , Table S3). According to our data, any retro‐aza‐Michael reaction was again unlikely 18a,28…”

“…Once substrate 17a had fully reacted, the yield and enantioselectivity were stable with time. Hence, according to these data, any retro‐aza‐Michael reaction was unlikely 18a,28. Finally, the plot of ln ( n reagent 17a ) versus time gave a curve that could not be fitted with a first‐order kinetic law by the linear least‐squares technique (Figure S2).…”

Dataset of polyoxometalate-assisted N-heterocyclic carbene gold(I) complexes

“…The complex [AuCl(I t Bu)] was prepared by reaction of a solution of HI t Bu + Cl − [10] , [11] (0.400 g, 1.845 mmol) in 60 mL of acetone with [AuCl(THT)] [7] , [8] (0.887 g, 2.767 mmol) and K 2 CO 3 (1.275 g, 9.225 mmol). Workup as described above for [AuCl(BIPr)] [5] afforded a white powder.…”