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

Publication ,  Journal Article
Timmerman, JC; Laulhé, S; Widenhoefer, RA
Published in: Organic letters
March 2017

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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Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2017

Volume

19

Issue

6

Start / End Page

1466 / 1469

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

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Timmerman, J. C., Laulhé, S., & Widenhoefer, R. A. (2017). Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones. Organic Letters, 19(6), 1466–1469. https://doi.org/10.1021/acs.orglett.7b00450
Timmerman, Jacob C., Sébastien Laulhé, and Ross A. Widenhoefer. “Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones.Organic Letters 19, no. 6 (March 2017): 1466–69. https://doi.org/10.1021/acs.orglett.7b00450.
Timmerman JC, Laulhé S, Widenhoefer RA. Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones. Organic letters. 2017 Mar;19(6):1466–9.
Timmerman, Jacob C., et al. “Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones.Organic Letters, vol. 19, no. 6, Mar. 2017, pp. 1466–69. Epmc, doi:10.1021/acs.orglett.7b00450.
Timmerman JC, Laulhé S, Widenhoefer RA. Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones. Organic letters. 2017 Mar;19(6):1466–1469.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2017

Volume

19

Issue

6

Start / End Page

1466 / 1469

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences