Volume 46, Issue 12 pp. 2074-2077

Communication

Rhodium-Catalyzed Cycloisomerization: Formation of Indoles, Benzofurans, and Enol Lactones^†

Barry M. Trost Prof.,

Barry M. Trost Prof.

[email protected]

Department of Chemistry, Stanford University, Stanford, CA 94305–5080, USA, Fax: (+1) 650-725-0259

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Andrew McClory,

Andrew McClory

Department of Chemistry, Stanford University, Stanford, CA 94305–5080, USA, Fax: (+1) 650-725-0259

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Barry M. Trost Prof.,

Barry M. Trost Prof.

[email protected]

Department of Chemistry, Stanford University, Stanford, CA 94305–5080, USA, Fax: (+1) 650-725-0259

Search for more papers by this author

Andrew McClory,

Andrew McClory

Department of Chemistry, Stanford University, Stanford, CA 94305–5080, USA, Fax: (+1) 650-725-0259

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First published: 02 March 2007

https://doi.org/10.1002/anie.200604183

Citations: 183

^†

We thank the National Science Foundation and the National Institutes of Health, General Medical Sciences Institute (GM 33049) for their generous support of our programs. Mass spectra were provided by the Mass Spectrometry Regional Center of the University of California, San Francisco, which is supported by the NIH Division of Research Resources.

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Graphical Abstract

Internal affairs: Indoles, benzofurans, and enol lactones are formed chemoselectively from the rhodium-catalyzed cycloisomerization reaction of easily prepared alkynyl aniline substrates (see scheme, cod=cycloocta-1,5-diene, DMF=N,N-dimethylformamide). The reaction may proceed by nucleophilic capture of a vinylidene intermediate. Indoles are formed under mild conditions using low catalyst loadings.

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Volume46, Issue12

March 12, 2007

Pages 2074-2077

Rhodium-Catalyzed Cycloisomerization: Formation of Indoles, Benzofurans, and Enol Lactones^†

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Rhodium-Catalyzed Cycloisomerization: Formation of Indoles, Benzofurans, and Enol Lactones†

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Rhodium-Catalyzed Cycloisomerization: Formation of Indoles, Benzofurans, and Enol Lactones^†