Highly Active Au(I) Catalyst for the Intramolecular exo-Hydrofunctionalization of Allenes with Carbon, Nitrogen, and Oxygen Nucleophiles

Zhibin Zhang, Cong Liu, Robert E. Kinder, Xiaoqing Han, Hua Qian and Ross A. Widenhoefer*

*P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, Email: rwidenhochem.duke.edu

Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc., 2006, 128, 9066-9073.

DOI: 10.1021/ja062045r

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Abstract

The Au(I)-catalyzed intramolecular hydroamination of N-allenyl carbamates was effective for the formation of various cyclic amines. γ-Hydroxy and δ-hydroxy allenes underwent Au-catalyzed intramolecular hydroalkoxylation to form the corresponding oxygen heterocycles in good yield. 2-Allenyl indoles underwent Au-catalyzed intramolecular hydroarylation to form 4-vinyl tetrahydrocarbazoles in good yield.

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Intermolecular Hydroamination of Allenes with N-Unsubstituted Carbamates Catalyzed by a Gold(I) N-Heterocyclic Carbene Complex

R. E. Kinder, Z. Zhang, R. A. Widenhoefer, Org. Lett., 2008, 10, 3157-3159.

Gold(I)-Catalyzed Intramolecular Hydroamination of Alkenyl Carbamates

X. Han, R. A. Widenhoefer, Angew. Chem. Int. Ed., 2006, 45, 1747-1749.

Platinum-Catalyzed Intramolecular Hydroalkoxylation of γ- and δ-Hydroxy Olefins to Form Cyclic Ethers

H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc., 2004, 126, 9536-9537.

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Key Words

Pyrrolidines, Piperidines, Cyclic Ethers

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ID: J48-Y2006-2220