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

Journal Article

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.

Full Text

Duke Authors

Cited Authors

  • Timmerman, JC; Laulhé, S; Widenhoefer, RA

Published Date

  • March 7, 2017

Published In

Volume / Issue

  • 19 / 6

Start / End Page

  • 1466 - 1469

PubMed ID

  • 28266212

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.7b00450

Language

  • eng