Prev. Article Next Article Table of Contents

Letter

Room Temperature Hydroamination of N-Alkenyl Ureas Catalyzed by a Gold(I) N-Heterocyclic Carbene Complex

Supporting Info

Christopher F. Bender and Ross A. Widenhoefer*

P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346

Org. Lett., 2006, 8 (23), pp 5303–5305

DOI: 10.1021/ol062107i

Publication Date (Web): October 14, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rwidenho@chem.duke.edu

Abstract

Treatment of an N-4-pentenyl or N-5-hexenyl urea with a catalytic 1:1 mixture of a gold(I) N,N-diaryl imidazol-2-ylidine complex and AgOTf at or near room temperature leads to intramolecular exo-hydroamination to form the corresponding nitrogen heterocycle in excellent yield.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue November 09, 2006
Received August 26, 2006

Recommend & Share

Related Content

Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated OlefinsJournal of the American Chemical Society
- Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins
  Junliang Zhang, Cai-Guang Yang, and Chuan He
  Journal of the American Chemical Society 2006 128 (6), pp 1798–1799
  Abstract: Ph₃PAuOTf catalyzes efficient intra- and intermolecular hydroamination of unactivated olefins with sulfonamides.
  Abstract | Full Text HTML | Hi-Res PDF
Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of AllenesJournal of the American Chemical Society
- Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of Allenes
  Rebecca L. LaLonde, Benjamin D. Sherry, Eun Joo Kang, and F. Dean Toste
  Journal of the American Chemical Society 2007 129 (9), pp 2452–2453
  Abstract: The asymmetric intramolecular hydroamination of allenes catalyzed by phosphinegold(I)−bis-p-nitrobenzoate complexes is described. This reaction is applicable to the enantioselective formation of vinyl pyrrolidines and piperidines in 70−99% ee.
  Abstract | Full Text HTML | Hi-Res PDF
Gold(I)-Catalyzed Enantioselective Hydroamination of N-Allenyl CarbamatesOrganic Letters
- Gold(I)-Catalyzed Enantioselective Hydroamination of N-Allenyl Carbamates
  Zhibin Zhang, Christopher F. Bender, and Ross A. Widenhoefer
  Organic Letters 2007 9 (15), pp 2887–2889
  Abstract: Treatment of the N-4,5-hexadienyl carbamate 2a with a catalytic 1:2 mixture of [(S)-1]Au₂Cl₂ [(S)-1 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgClO₄ in m-xylene at −40 °C for 24 h led to isolation of 2-vinylpyrrolidine 3a in 97% yield with 81% ee. Gold(I)-...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Room Temperature Hydroamination of N-Alkenyl Ureas Catalyzed by a Gold(I) N-Heterocyclic Carbene Complex

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins

Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of Allenes

Gold(I)-Catalyzed Enantioselective Hydroamination of N-Allenyl Carbamates

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES