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AuCl3-Catalyzed Benzannulation: Synthesis of Naphthyl Ketone Derivatives from o-Alkynylbenzaldehydes with Alkynes
Abstract
The reaction of o-alkynylbenzaldehydes 1 and alkynes 2 in the presence of a catalytic amount of AuCl3 in (CH2Cl)2 at 80 degrees C gave naphthyl ketone products in high yields. The AuCl3-catalyzed formal [4 + 2] benzannulation proceeds most probably through the coordination of the triple bond of 1 to AuCl3, the formation of benzo[c]pyrylium auric ate complex via the nucleophilic addition of the carbonyl oxygen atom, the Diels-Alder addition of alkynes 2 to the auric ate complex, and subsequent bond rearrangement. Similarly, the AuCl3-catalyzed reactions of o-alkynylacetophenone and o-alkynylbenzophenone with phenylacetylene afforded the corresponding naphthyl ketone products in good yields.
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Citations
Cited by
Hashmi, A. S. K., & Hutchings, G. J. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200602454 · Cited by 3,423
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Catalytic Carbophilic Activation: Catalysis by Platinum and Gold π Acids
Fürstner, A., & Davies, P. W. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200604335 · Cited by 2,332
Ligand Effects in Homogeneous Au Catalysis
Gorin, D. J., Sherry, B. D., & Toste, F. D. (2008) · Chemical Reviews · doi:10.1021/cr068430g · Cited by 2,051
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Corma, A., & Garcia, H. (2008) · Chemical Society Reviews · doi:10.1039/b707314n · Cited by 1,883
Metadata
- Authors
- Asao, N., Takahashi, K., Lee, S., Kasahara, T., & Yamamoto, Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-10-01
- Volume
- 124
- Issue
- 43
- Pages
- 12650-12651
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2139383250
- Cited by
- 427
- References
- 0
- FWCI
- 10.76
- Type
- journal article
- Language
- en
- Open access
- closed
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- Asao, N., Takahashi, K., Lee, S., Kasahara, T., & Yamamoto, Y. (2002). AuCl3-Catalyzed Benzannulation: Synthesis of Naphthyl Ketone Derivatives from o-Alkynylbenzaldehydes with Alkynes. Journal of the American Chemical Society. https://doi.org/10.1021/ja028128z
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