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 (free Supporting Information)
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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R. E. Kinder, Z. Zhang, R. A. Widenhoefer, Org. Lett., 2008, 10, 3157-3159.
X. Han, R. A. Widenhoefer, Angew. Chem. Int. Ed., 2006, 45, 1747-1749.
H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc., 2004, 126, 9536-9537.