Palladium-catalyzed ring expansion reaction of 1-alkynylcyclobutanols with aryl iodides: An efficient route to 2-disubstituted methylenecyclopentanones

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 595-597

  Wei, Li Mei ^a,b   Wei, Li Lan ^a,b   Pan, Wen Bin ^a,b   Wu, Ming Jung ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b FOOYIN UNIVERSITY   (Taiwan)

Author keywords

Cyclopentanones; Palladium and compounds; Ring expansion

Indexed keywords

ACETONITRILE; ALCOHOL DERIVATIVE; CARBON; CYCLOPENTANONE DERIVATIVE; IODINE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

INSERTION SEQUENCES;

EID: 0037433931     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02581-9     Document Type: Article

References (16)

1. For some recent works on palladium-catalyzed ring expansion of cyclobutanols: see (a) Clark, G. R.; Thiensathit, S. Tetrahedron Lett. 1985, 26, 2503-2506; (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957-3962; (c) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908-7910; (d) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296; (e) Nemoto, H.; Miyata, J.; M.; Fukumoto, K. Tetrahedron 1996, 52, 10363-10374; (f) Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857.
2. For some recent works on palladium-catalyzed ring expansion of cyclobutanols: see (a) Clark, G. R.; Thiensathit, S. Tetrahedron Lett. 1985, 26, 2503-2506; (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957-3962; (c) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908-7910; (d) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296; (e) Nemoto, H.; Miyata, J.; M.; Fukumoto, K. Tetrahedron 1996, 52, 10363-10374; (f) Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857.
3. For some recent works on palladium-catalyzed ring expansion of cyclobutanols: see (a) Clark, G. R.; Thiensathit, S. Tetrahedron Lett. 1985, 26, 2503-2506; (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957-3962; (c) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908-7910; (d) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296; (e) Nemoto, H.; Miyata, J.; M.; Fukumoto, K. Tetrahedron 1996, 52, 10363-10374; (f) Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857.
4. For some recent works on palladium-catalyzed ring expansion of cyclobutanols: see (a) Clark, G. R.; Thiensathit, S. Tetrahedron Lett. 1985, 26, 2503-2506; (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957-3962; (c) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908-7910; (d) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296; (e) Nemoto, H.; Miyata, J.; M.; Fukumoto, K. Tetrahedron 1996, 52, 10363-10374; (f) Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857.
5. For some recent works on palladium-catalyzed ring expansion of cyclobutanols: see (a) Clark, G. R.; Thiensathit, S. Tetrahedron Lett. 1985, 26, 2503-2506; (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957-3962; (c) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908-7910; (d) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296; (e) Nemoto, H.; Miyata, J.; M.; Fukumoto, K. Tetrahedron 1996, 52, 10363-10374; (f) Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857.
6. For some recent works on palladium-catalyzed ring expansion of cyclobutanols: see (a) Clark, G. R.; Thiensathit, S. Tetrahedron Lett. 1985, 26, 2503-2506; (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957-3962; (c) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908-7910; (d) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296; (e) Nemoto, H.; Miyata, J.; M.; Fukumoto, K. Tetrahedron 1996, 52, 10363-10374; (f) Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857.
7. Recently, Uemura et al. reported a palladium-catalyzed oxidative ring cleavage reaction of cyclobutanols: (a) Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645-2646; (b) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010-11011; (c) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2000, 122, 12049-12050.
8. Recently, Uemura et al. reported a palladium-catalyzed oxidative ring cleavage reaction of cyclobutanols: (a) Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645-2646; (b) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010-11011; (c) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2000, 122, 12049-12050.
9. Recently, Uemura et al. reported a palladium-catalyzed oxidative ring cleavage reaction of cyclobutanols: (a) Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645-2646; (b) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010-11011; (c) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2000, 122, 12049-12050.
10. Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;6450-6451.
11. Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583-8586.
12. Yoshida M., Sugimoto K., Ihara M. Tetrahedron Lett. 41:2000;5089-5092.
13. Wu M.-J., Wei L.-M., Lin C.-F., Leou S.-P., Wei L.-L. Tetrahedron. 57:2000;7839-7844.
14. +, 2), 158(89), 143(41), 115(100).
15. 20O: C, 86.92; H, 7.29. Found: C, 86.75; H, 7.36.
16. 2=0.2185. Diffractometer: Bruker SMART APEX. Crystallographic data (excluding structure factors) for this structure have been deposited at the Cambridge Crystallographic Data centre as supplementary publication no. CCDC-190286, and may be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).