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Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles.

Publication ,  Journal Article
Zhang, Z; Liu, C; Kinder, RE; Han, X; Qian, H; Widenhoefer, RA
Published in: Journal of the American Chemical Society
July 2006

Reaction of benzyl (2,2-diphenyl-4,5-hexadienyl)carbamate (4) with a catalytic 1:1 mixture of Au[P(t-Bu)2(o-biphenyl)]Cl (2) and AgOTf (5 mol %) in dioxane at 25 degrees C for 45 min led to isolation of benzyl 4,4-diphenyl-2-vinylpyrrolidine-1-carboxylate (5) in 95% yield. The Au(I)-catalyzed intramolecular hydroamination of N-allenyl carbamates tolerated substitution at the alkyl and allenyl carbon atoms and was effective for the formation of piperidine derivatives. gamma-Hydroxy and delta-hydroxy allenes also underwent Au-catalyzed intramolecular hydroalkoxylation within minutes at room temperature to form the corresponding oxygen heterocycles in good yield with high exo-selectivity. 2-Allenyl indoles underwent Au-catalyzed intramolecular hydroarylation within minutes at room temperature to form 4-vinyl tetrahydrocarbazoles in good yield. Au-catalyzed cyclization of N-allenyl carbamates, allenyl alcohols, and 2-allenyl indoles that possessed an axially chiral allenyl moiety occurred with transfer of chirality from the allenyl moiety to the newly formed stereogenic tetrahedral carbon atom.

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Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

July 2006

Volume

128

Issue

28

Start / End Page

9066 / 9073

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Chicago
ICMJE
MLA
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Zhang, Z., Liu, C., Kinder, R. E., Han, X., Qian, H., & Widenhoefer, R. A. (2006). Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles. Journal of the American Chemical Society, 128(28), 9066–9073. https://doi.org/10.1021/ja062045r
Zhang, Zhibin, Cong Liu, Robert E. Kinder, Xiaoqing Han, Hua Qian, and Ross A. Widenhoefer. “Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles.Journal of the American Chemical Society 128, no. 28 (July 2006): 9066–73. https://doi.org/10.1021/ja062045r.
Zhang Z, Liu C, Kinder RE, Han X, Qian H, Widenhoefer RA. Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles. Journal of the American Chemical Society. 2006 Jul;128(28):9066–73.
Zhang, Zhibin, et al. “Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles.Journal of the American Chemical Society, vol. 128, no. 28, July 2006, pp. 9066–73. Epmc, doi:10.1021/ja062045r.
Zhang Z, Liu C, Kinder RE, Han X, Qian H, Widenhoefer RA. Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles. Journal of the American Chemical Society. 2006 Jul;128(28):9066–9073.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

July 2006

Volume

128

Issue

28

Start / End Page

9066 / 9073

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences