Rhodium-catalyzed isomerization of α-arylpropargyl alcohols to indanones: Involvement of an unexpected reaction cascade

Journal of the American Chemical Society

Volumn 127, Issue 9, 2005, Pages 2872-2873

  Shintani, Ryo ^a   Okamoto, Kazuhiro ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; INDANONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHROMATOGRAPHY; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION;

EID: 14844291349     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042582g     Document Type: Article

References (25)

1. For reviews, see: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1. (b) Fairlamb, I. J. S. Angew. Chem., Int. Ed. 2004, 43, 1048. (c) Uma, R.; Crévisy, C.; Grée, R. Chem. Rev. 2003, 103, 27.
2. For reviews, see: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1. (b) Fairlamb, I. J. S. Angew. Chem., Int. Ed. 2004, 43, 1048. (c) Uma, R.; Crévisy, C.; Grée, R. Chem. Rev. 2003, 103, 27.
3. For reviews, see: (a) Trost, B. M.; Krische, M. J. Synlett 1998, 1. (b) Fairlamb, I. J. S. Angew. Chem., Int. Ed. 2004, 43, 1048. (c) Uma, R.; Crévisy, C.; Grée, R. Chem. Rev. 2003, 103, 27.
4. Saïah, M. K. E.; Pellicciari, R. Tetrahedron Lett. 1995, 36, 4497.
5. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
6. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
7. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
8. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
9. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
10. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
11. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
12. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
13. Several examples of propargyl alcohol isomerizations catalyzed by other transition metals have been reported. Ruthenium catalysis: (a) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586. (b) Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890. (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531. Iridium catalysis: (d) Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109. Palladium catalysis: (e) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259. (f) Guo, C.; Lu, X. Synlett 1992, 405. Rhenium catalysis: (g) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron 1992, 48, 2059. See also: (h) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654. (i) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
14. In some cases, we have obtained partially desilylated indanones when trimethylsilyl-substituted substrates are used.
15. Due to the basic aqueous media, an H-D exchange at the α-position occurs to lower the D-content at higher conversions.
16. Treatment of a chlororhodium complex with aqueous KOH is known to produce a hydroxorhodium species. For examples, see: (a) Grushin, V. V.; Kuznetsov, V. F.; Bensimon, C.; Alper, H. Organometallics 1995, 14, 3927. (b) Uson, R.; Oro, L. A.; Cabeza, J. A. Inorg. Synth. 1985, 23, 126.
17. Treatment of a chlororhodium complex with aqueous KOH is known to produce a hydroxorhodium species. For examples, see: (a) Grushin, V. V.; Kuznetsov, V. F.; Bensimon, C.; Alper, H. Organometallics 1995, 14, 3927. (b) Uson, R.; Oro, L. A.; Cabeza, J. A. Inorg. Synth. 1985, 23, 126.
18. For examples of a formation of an arylrhodium species involving a 1,4-hydrogen shift, see: (a) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (b) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
19. For examples of a formation of an arylrhodium species involving a 1,4-hydrogen shift, see: (a) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (b) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
20. In an intermolecular system, we reported a mechanism involving a formation of an oxa-π-allylrhodium complex by the addition of a phenylrhodium species to an enone and its hydrolysis to give a hydroxorhodium complex and a 1,4-addition product: Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
21. Under the catalytic reaction conditions, trans-1-phenyl-3-triethylsilyl- 2-propen-1-one (3b) does not produce indanone 2b, thereby eliminating the possibility of a Nazarov-cyclization mechanism.
22. 1H NMR at 6% conversion.
23. 1H NMR analyses, see: Adams, C. S.; Legzdins, P.; McNeil, W. S. Organometallics 2001, 20, 4939.
24. 1H NMR at 4% conversion.
25. 2 (which usually results in the formation of rhodium-black).