Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones.

The cationic gold phosphine complex [(P1)Au(NCMe)]⁺SbF₆^- [P1 = P(t-Bu)₂o-biphenyl; 2] catalyzes the intramolecular hydroamination of 6-alkenyl-2-pyridones to form 1,6-carboannulated 2-pyridones in high yield. The hydroamination of 6-(γ-alkenyl)-2-pyridones was effective for monosubstituted and 1,1- and 1,2-disubstituted aliphatic alkenes, and the method was likewise effective for the hydroamination of 6-(δ-alkenyl)-2-pyridones. Spectroscopic analysis of mixtures of 6-(3-butenyl)-2-pyridone, (P1)AuCl, and AgSbF₆ established the N-bound 2-hydroxypyridine complex [(P1)Au(NC₆H₃-2-OH-6-CH₂CH₂CH═CH₂)]⁺ SbF₆^- as the catalyst resting state.

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Author Ross A. Widenhoefer Chemistry