Rhodium-catalyzed tandem cyclization: Formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media

Journal of Organic Chemistry

Volumn 69, Issue 14, 2004, Pages 4607-4614

  Lautens, Mark ^a   Marquardt, Tzvetelina ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSIS; ESTERS; INDENTATION; OLEFINS; RHODIUM COMPOUNDS;

ARYLBORONATE ESTERS; TANDEM CYCLIZATION; TRANSMETALATION;

CASCADE CONNECTIONS;

1H INDENE DERIVATIVE; ACETYLENE; ALKENE; BORIC ACID; BORONIC ACID DERIVATIVE; INDAN DERIVATIVE; INDENE DERIVATIVE; RHODIUM; TRI TERT BUTYLPHOSPHONIUM TETRAFLUOROBORATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON; LINKAGE ANALYSIS; MICHAEL ADDITION; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 3042780057     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049722p     Document Type: Article

References (37)

1. For rewiews of organic synthesis in water, see: (a) Grieco, P. A. Organic Synthesis in Water; Blackie Academic and Professional: London, 1998.
2. (b) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998.
3. (c) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; Wiley-Interscience: New York, 1997.
4. (d) Horváth, I. T.; Joó, F. Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic: Dordrecht, The Niederlands, 1995.
5. (e) Li, C. J. Chem. Rev. 1993, 93, 2023.
6. (f) Li, C. J.; Chan, T. H. Tetrahedron 1999, 93, 2023.
7. (g) For a general review on rhodium-catalyzed carbon-carbon bond-forming reactions of organometallic compounds, see: Fagnou, K.; Lautens, M. Chem Rev. 2003, 103, 169.
8. For addition to enones: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229.
9. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
10. (c) For a review, see: Hayashi, T. Synlett 2001, 879.
11. Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
12. (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358.
13. Other examples for reactions using TPPDS, see: (a) Thorpe, T.; Brown, S. M.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2000, 41, 4503.
14. (b) Chen, H.; Li, Y.; Chen, J.; Cheng, P.; Li, X. Catal. Today 2002, 74, 131.
15. (a) Lautens, M.; Yoshida, M.Org. Lett. 2002, 4, 123.
16. (b) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
17. (c) Recently, Hayashi has reported a similar addition of alkynes: Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
18. Lautens, M.; Mancuso, J. Org. Lett. 2002, 4, 2105.
19. (a) Maguire, A. R.; Papot, S.; Ford, A.; Touhey, S.; O'Connor, R.; Clynes, M. Synlett 2001, 1, 41.
20. (b) Karaguni, I.-M.; Herter, P.; Courzoulidou, E.; Carpintero, M.; Müller, O.; Waldmann, H. German Patent DE 101 63 426.9, 2003.
21. Selected references: (a) Giardellio, R. M.; Hamilton, S. R.; Krush, A. J. N. Engl. J. Med. 1993, 328, 1313.
22. (b) Heath, C. W.; Thun, M. J.; Greeberg, E. R.; Levin, B.; Marnett, L. J. Cancer 1994, 74, 2885.
23. (c) Pepin, P.; Bouchard, L.; Nicole, P.; Castonguay, A. Carcinogenesis 1992, 13, 341.
24. (d) Rao, C. V.; Rivenson, A.; Simi, B.; Zang, E.; Kelloff, G.; Steele, V.; Reddy, B. S. Cancer Res. 1995, 55, 1464.
25. (e) Thompson, H. J.; Jiang, C.; Lu, J.; Menta, R. G.; Piazza, G. A.; Paranka, N. S.; Pamukcu, R.; Ahnen, D. J. Cancer Res. 1997, 57, 6.
26. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 26, 4295.
27. Piers, E.; Chong, J. M.; Morton, H. E. Tetrahedron 1989, 45, 363.
28. Kaiser, F.; Schwink, L.; Valzer, J.; Schmalz, H.-G. J. Org. Chem. 2002, 67, 9248.
29. Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316.
30. Kumar, S. J. Chem. Soc., Perkin Trans. 1 2001, 1018.
31. Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527.
32. Compound 41 was synthesized by Sonogashira coupling of 2-bromoiodobenzene and phenylacetylene and further application of our standard protocol for obtaining the corresponding boronate ester derivative.
33. Joó, F.; Kovács, J.; Bényei, A. C.; Nádasdi, L.; Laurenczy, G. Chem. Eur. J. 2001, 7, 193.
34. Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
35. The addition of fluoride may also promote the formation of a catalytically active fluororhodium(I) intermediate.
36. (a) For preparation of t-Bu-amphos-Cl 3 and an account of its efficiency for Pd-catalyzed Suzuki couplings in aqueous media, see: Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757.
37. (b) Original amphos ligand: Smith, R. T.; Baird, M. C. Inorg. Chim. Acta 1982, 62, 135.