Synthesis of Seven-Membered-Ring Ketones by Arylative Ring Expansion of Alkyne-Substituted Cyclobutanones†
Takanori Matsuda Dr.
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615–8510, Japan, Fax: (+81) 75-383-2748
Search for more papers by this authorMasaomi Makino
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615–8510, Japan, Fax: (+81) 75-383-2748
Search for more papers by this authorMasahiro Murakami Prof. Dr.
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615–8510, Japan, Fax: (+81) 75-383-2748
Search for more papers by this authorTakanori Matsuda Dr.
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615–8510, Japan, Fax: (+81) 75-383-2748
Search for more papers by this authorMasaomi Makino
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615–8510, Japan, Fax: (+81) 75-383-2748
Search for more papers by this authorMasahiro Murakami Prof. Dr.
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615–8510, Japan, Fax: (+81) 75-383-2748
Search for more papers by this authorThis work was supported by a Grant-in-Aid for Young Scientists (B; No. 15750085) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.
Graphical Abstract
Wachsende Kreise: Siebenringketone werden durch Rhodium(I)-katalysierte arylierende Ringerweiterung aus Alkin-substituierten Arylcyclobutanonen gebildet. Dabei laufen zwei C-C-Verknüpfungen und ein C-C-Bindungsbruch nacheinander ab (siehe Schema).
Supporting Information
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References
- 1
- 1aN. A. Petasis, M. A. Patane, Tetrahedron 1992, 48, 5757–5821;
- 1bC. J. Roxburgh, Tetrahedron 1993, 49, 10 749–10 784;
- 1cG. Mehta, V. Singh, Chem. Rev. 1999, 99, 881–930;
- 1dL. Yet, Chem. Rev. 2000, 100, 2963–3007.
- 2
- 2aG. Illuminati, L. Mandolini, Acc. Chem. Res. 1981, 14, 95–102;
- 2bC. Galli, L. Mandolini, Eur. J. Org. Chem. 2000, 3117–3125.
- 3
- 3aT. Matsuda, M. Makino, M. Murakami, Org. Lett. 2004, 6, 1257–1259;
- 3bT. Matsuda, M. Makino, M. Murakami, Bull. Chem. Soc. Jpn. 2005, in press.
- 4For intramolecular additions of an organorhodium(I) to a carbonyl group, see:
- 4aA. Takezawa, K. Yamaguchi, T. Ohmura, Y. Yamamoto, N. Miyaura, Synlett 2002, 1733–1735;
- 4bR. Shintani, K. Okamoto, Y. Otomaru, K. Ueyama, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 54–55;
- 4cT. Miura, T. Sasaki, H. Nakazawa, M. Murakami, J. Am. Chem. Soc. 2005, 127, 1390–1391;
- 4dT. Miura, M. Shimada, M. Murakami, Synlett 2005, 667–669; For intermolecular additions, see:
- 4eM. Sakai, M. Ueda, M. Miyaura, Angew. Chem. 1998, 110, 3475–3477;
10.1002/(SICI)1521-3757(19981204)110:23<3475::AID-ANGE3475>3.0.CO;2-W Web of Science® Google ScholarAngew. Chem. Int. Ed. 1998, 37, 3279–3281;10.1002/(SICI)1521-3773(19981217)37:23<3279::AID-ANIE3279>3.0.CO;2-M CAS PubMed Web of Science® Google Scholar
- 4fC. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1674–1679;
- 4gM. Pucheault, S. Darses, J.-P. Genet, J. Am. Chem. Soc. 2004, 126, 15 356–15 357.
- 5Wittig olefination of the aldehyde with cyclopropylidenephosphorane afforded 2-bromobenzylidenecyclopropane (71 %). Oxidation of the methylenecyclopropane with m-chloroperbenzoic acid followed by treatment with aqueous HBF4 gave 2-(2-bromophenyl)cyclobutanone (58 %). Introduction of a but-1-ynyl moiety by palladium-catalyzed coupling furnished 1 a (55 %). See Supporting Information for details.
- 6Triphenylboroxin and water were used to generate phenylboronic acid in situ, see:
- 6aT. Senda, M. Ogasawara, T. Hayashi, J. Org. Chem. 2001, 66, 6852–6856;
- 6bT. Hayashi, K. Inoue, N. Taniguchi, M. Ogasawara, J. Am. Chem. Soc. 2001, 123, 9918–9919.
- 7
- 7aM. Murakami, H. Igawa, Helv. Chim. Acta 2002, 85, 4182–4188;
- 7bM. Lautens, M. Yoshida, Org. Lett. 2002, 4, 123–125;
- 7cM. Lautens, T. Marquardt, J. Org. Chem. 2004, 69, 4607–4614;
- 7dT. Miura, M. Shimada, M. Murakami, J. Am. Chem. Soc. 2005, 127, 1094–1095.
- 8For a review on β-carbon eliminations from palladium(II) cyclobutanolates, see: T. Nishimura, S. Uemura, Synlett 2004, 201–216.
- 9For examples of related migrations of transition metals leading to enolates, see:
- 9aH. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2003, 125, 2056–2057;
- 9bS. V. Gagnier, R. C. Larock, J. Am. Chem. Soc. 2003, 125, 4804–4807.
- 10
- 10aK. Oguma, M. Miura, T. Satoh, M. Nomura, J. Am. Chem. Soc. 2000, 122, 10 464–10 465;
- 10bR. Shintani, K. Okamoto, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 2872–2873;
- 10cH. Yamabe, A. Mizuno, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 3248–3249.
- 11The reaction with o-tolylboroxin resulted in the formation of a complex mixture of products, in which 1,2-adduct 4 was the only identifiable product.
- 12Ring expansion by β-carbon elimination failed to occur even when the isolated 5 ja was heated at 160 °C in the presence of the rhodium catalyst.
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