Synthesis of Indanes through Coupling of Ethynylstyrene Derivatives with Carbene Complexes

Organometallics

Volumn 23, Issue 6, 2004, Pages 1231-1235

  Zhang, Lei ^a   Herndon, James W ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; ELECTROPHILICITY;

CARBON MONOXIDE; CHROMATOGRAPHIC ANALYSIS; COMPLEXATION; DERIVATIVES; HYDROGEN; MIXTURES; SILICA GEL; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

EID: 1842534002     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034334j     Document Type: Article

References (37)

1. Herndon, J. W.; Zhang, Y.; Wang, H.; Wang, K. Tetrahedron Lett. 2000, 41, 8687-8690.
2. (b) Herndon, J. W.; Hayford, A. Organometallics 1995, 14, 1556-1558.
3. (c) Waters, M. A.; Bos, M. E.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 6403-6413.
4. Jackson, T. J.; Herndon, J. W. Tetrahedron 2001, 57, 3859-3868.
5. Challener, C. A.; Wulff, W. D.; Anderson, B. A.; Chamberlin, S.; Faron, K. L.; Kim, O. K.; Murray, C. K.; Xu, Y. C.; Yang, D. C.; Darling, S. D. J. Am. Chem. Soc. 1993, 115, 1359-1376.
6. Turner, S. U.; Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1992, 114, 8394-8404.
7. This is a critical event in successful benzannulation reactions. Bos, M. E.; Wulff, W. D.; Miller, R. A.; Chamberlin, S.; Brandvold, T. A. J. Am. Chem. Soc. 1991, 113, 9293-9319.
8. Herndon, J. W. Tetrahedron 2000, 56, 1257-1280.
9. Indenes are the major products from coupling of amino(aryl)-carbene-chromium complexes and alkynes. (a) Yamashita, A. Tetrahedron Lett. 1986, 27, 5915-5918. (b) Döta, K. H.; Erben, H. G.; Harms, K. J. Chem. Soc., Chem. Commun. 1980, 692-693.
10. Indenes are the major products from coupling of amino(aryl)-carbene-chromium complexes and alkynes. (a) Yamashita, A. Tetrahedron Lett. 1986, 27, 5915-5918. (b) Döta, K. H.; Erben, H. G.; Harms, K. J. Chem. Soc., Chem. Commun. 1980, 692-693.
11. Indenes have also been prepared from the coupling of carbene complexes in mechanistically unrelated processes, (a) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2001, 123, 11113-11114. (b) Barluenga, J.; Trabanco, A. A.; Florez, J.; Garcia-Granda, S.; LLorca, M. A. J. Am. Chem. Soc. 1998, 120, 12129-12130.
12. Indenes have also been prepared from the coupling of carbene complexes in mechanistically unrelated processes, (a) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2001, 123, 11113-11114. (b) Barluenga, J.; Trabanco, A. A.; Florez, J.; Garcia-Granda, S.; LLorca, M. A. J. Am. Chem. Soc. 1998, 120, 12129-12130.
13. Examples in the 21st century: (a) Lowe, D. B.; Wickens, P. L.; Ma, X.; Zhang, M.; Bullock, W. H.; Coish, P. D. G.; Mugge, I. A.; Stolle, A.; Wang, M.; Wang, Y.; Zhang, C.; Zhang, H. J.; Zhu, L.; Tsutsumi, M.; Livingston, J. N. PCT Int. Appl. 2003, Chem. Abstr. 2003, 138, 153524. (b) Uchikawa, O.; Fukatsu, K.; Tokunoh, R.; Kawada, M.; Matsumoto, K.; Imai, Y.; Hinuma, S.; Kato, K.; Nishikawa, H.; Hirai, K.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4222-4239. (c) Fukatsu, K.; Uchikawa, O.; Kawada, M.; Yamano, T.; Yamashita, M. ; Kato, K.; Hirai, K.; Hinuma, S.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4212-4221. (d) Menander, K. B.; Mayle, M. J. PCT Int. Appl. 2000, Chem. Abstr. 2000, 133, 144943.
14. Examples in the 21st century: (a) Lowe, D. B.; Wickens, P. L.; Ma, X.; Zhang, M.; Bullock, W. H.; Coish, P. D. G.; Mugge, I. A.; Stolle, A.; Wang, M.; Wang, Y.; Zhang, C.; Zhang, H. J.; Zhu, L.; Tsutsumi, M.; Livingston, J. N. PCT Int. Appl. 2003, Chem. Abstr. 2003, 138, 153524. (b) Uchikawa, O.; Fukatsu, K.; Tokunoh, R.; Kawada, M.; Matsumoto, K.; Imai, Y.; Hinuma, S.; Kato, K.; Nishikawa, H.; Hirai, K.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4222-4239. (c) Fukatsu, K.; Uchikawa, O.; Kawada, M.; Yamano, T.; Yamashita, M. ; Kato, K.; Hirai, K.; Hinuma, S.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4212-4221. (d) Menander, K. B.; Mayle, M. J. PCT Int. Appl. 2000, Chem. Abstr. 2000, 133, 144943.
15. Examples in the 21st century: (a) Lowe, D. B.; Wickens, P. L.; Ma, X.; Zhang, M.; Bullock, W. H.; Coish, P. D. G.; Mugge, I. A.; Stolle, A.; Wang, M.; Wang, Y.; Zhang, C.; Zhang, H. J.; Zhu, L.; Tsutsumi, M.; Livingston, J. N. PCT Int. Appl. 2003, Chem. Abstr. 2003, 138, 153524. (b) Uchikawa, O.; Fukatsu, K.; Tokunoh, R.; Kawada, M.; Matsumoto, K.; Imai, Y.; Hinuma, S.; Kato, K.; Nishikawa, H.; Hirai, K.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4222-4239. (c) Fukatsu, K.; Uchikawa, O.; Kawada, M.; Yamano, T.; Yamashita, M. ; Kato, K.; Hirai, K.; Hinuma, S.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4212-4221. (d) Menander, K. B.; Mayle, M. J. PCT Int. Appl. 2000, Chem. Abstr. 2000, 133, 144943.
16. Examples in the 21st century: (a) Lowe, D. B.; Wickens, P. L.; Ma, X.; Zhang, M.; Bullock, W. H.; Coish, P. D. G.; Mugge, I. A.; Stolle, A.; Wang, M.; Wang, Y.; Zhang, C.; Zhang, H. J.; Zhu, L.; Tsutsumi, M.; Livingston, J. N. PCT Int. Appl. 2003, Chem. Abstr. 2003, 138, 153524. (b) Uchikawa, O.; Fukatsu, K.; Tokunoh, R.; Kawada, M.; Matsumoto, K.; Imai, Y.; Hinuma, S.; Kato, K.; Nishikawa, H.; Hirai, K.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4222-4239. (c) Fukatsu, K.; Uchikawa, O.; Kawada, M.; Yamano, T.; Yamashita, M. ; Kato, K.; Hirai, K.; Hinuma, S.; Miyamoto, M.; Ohkawa, S. J. Med. Chem. 2002, 45, 4212-4221. (d) Menander, K. B.; Mayle, M. J. PCT Int. Appl. 2000, Chem. Abstr. 2000, 133, 144943.
17. For a review of indane syntheses, see: Hong, B. C.; Sarshar, S. Org. Prep. Proc. Int. 1999, 31, 1-86.
18. This effect is dramatically illustrated in the following papers: (a) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (b) Hoye, T. R.; Rehberg, G. M. Organometallics 1989, 8, 2070-2071, (c) Korkowski, P. F.; Hoye, T. R.; Rydberg, D. B. J. Am. Chem. Soc. 1988, 110, 2676-2678.
19. This effect is dramatically illustrated in the following papers: (a) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (b) Hoye, T. R.; Rehberg, G. M. Organometallics 1989, 8, 2070-2071, (c) Korkowski, P. F.; Hoye, T. R.; Rydberg, D. B. J. Am. Chem. Soc. 1988, 110, 2676-2678.
20. This effect is dramatically illustrated in the following papers: (a) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (b) Hoye, T. R.; Rehberg, G. M. Organometallics 1989, 8, 2070-2071, (c) Korkowski, P. F.; Hoye, T. R.; Rydberg, D. B. J. Am. Chem. Soc. 1988, 110, 2676-2678.
21. Additional factors may influence benzannulation vs cyclopentannulation since the regioselectivity of alkyne insertion is different for the two processes. Waters, M. L.; Bos, M. E.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 6403-6413.
22. Barluenga, J.; Lopez, S.; Trabanco, A. A.; Florez, J. Chem. Eur. J. 2001, 7, 4723-4729.
23. For recent uses of phenoxycarbene complexes see: Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D.; Rheingold, A. L. Organometallics 1998, 17, 4298-4308.
24. Kamal de Fonseka, K.; Manning, C.; McCullough, J. J.; Yarwood, A. J. J. Am. Chem. Soc. 1977, 99, 8257-8261.
25. Formation of ring-opened products from similar carbocation intermediates can proceed with variable degrees of ring opening, (a) For an example where the degree of ring opening is controlled through reaction conditions see: Sarel, S. ; Breuer, E.; Ertag, S.; Salamon, R. Isr. J. Chem. 1963, 1, 451-459. (b) For an example involving only ring opening see: Kanemoto, S.; Shimizu, M.; Yoshioka, H. Bull. Chem. Soc. Jpn. 1989, 62, 2024-2031. (c) For examples involving no ring opening see: Traas, P. C.; Boelens, H.; Takken, H. J. Rec. Trav. Chim. 1976, 95, 57-66.
26. Formation of ring-opened products from similar carbocation intermediates can proceed with variable degrees of ring opening, (a) For an example where the degree of ring opening is controlled through reaction conditions see: Sarel, S. ; Breuer, E.; Ertag, S.; Salamon, R. Isr. J. Chem. 1963, 1, 451-459. (b) For an example involving only ring opening see: Kanemoto, S.; Shimizu, M.; Yoshioka, H. Bull. Chem. Soc. Jpn. 1989, 62, 2024-2031. (c) For examples involving no ring opening see: Traas, P. C.; Boelens, H.; Takken, H. J. Rec. Trav. Chim. 1976, 95, 57-66.
27. Formation of ring-opened products from similar carbocation intermediates can proceed with variable degrees of ring opening, (a) For an example where the degree of ring opening is controlled through reaction conditions see: Sarel, S. ; Breuer, E.; Ertag, S.; Salamon, R. Isr. J. Chem. 1963, 1, 451-459. (b) For an example involving only ring opening see: Kanemoto, S.; Shimizu, M.; Yoshioka, H. Bull. Chem. Soc. Jpn. 1989, 62, 2024-2031. (c) For examples involving no ring opening see: Traas, P. C.; Boelens, H.; Takken, H. J. Rec. Trav. Chim. 1976, 95, 57-66.
28. Indene double-bond isomerization can be catalyzed by base or thermolysis, (a) For thermal interconveraion, see: Roth, W. R. Tetrahedron Lett. 1964, 1009-1013. (b) For base-catalyzed rearrangement, see: Bergson, J.; Weidler, A. M. Acta Chim. Scand. 1964, 18, 1487-1497.
29. Indene double-bond isomerization can be catalyzed by base or thermolysis, (a) For thermal interconveraion, see: Roth, W. R. Tetrahedron Lett. 1964, 1009-1013. (b) For base-catalyzed rearrangement, see: Bergson, J.; Weidler, A. M. Acta Chim. Scand. 1964, 18, 1487-1497.
30. (a) An attempt to induce isomerization of indenes by acid failed. Christol, H.; Plenat, M. F.; Huebner, C. F. Bull. Soc. Chim. Fr. 1964, 2640-2643.
31. (b) Acid-catalyzed isomerization of 16j might have occurred because of the intermediacy of cyclopropylcarbinyl cation intermediates. Richey, H. G., Jr. In Carbonium Ions; Olah, G. A., Schleyer, P. von R., Eds.; Wiley-Interscience: New York, 1972; Vol. 3, pp 1201-1294.
32. Obtained from an MM2 calculation using CHEM 3D.
33. Oullette, R. J.; Baron, D.; Stolfo, J.; Rosenblum, A.; Weber, P. Tetrahedron 1972, 28, 2163-2181.
34. (a) A similar stabilization was suggested to explain the unique regioselectivity exhibited in the coupling of stannylacetylenes and chromium carbene complexes. Although this effect was more strongly noted for tin than for silicon, it is still important for silicon; TMS is much larger than propyl, yet propyl ends up α to OH in the major product of benzannulations using pentynyltrimethylsilane. Chamberlin, S.; Waters, M. L.; Wulff, W. D. J. Am. Chem. Soc. 1994, 116, 3113-3114.
35. (b) Later studies showed that a similar effect may be operative for alkynylboranes. Davies, M. W.; Johnson, C. N.; Harrity, J. P. A. J. Org. Chem. 2001, 66, 3525-3532.
36. Jiang, W.; Fuertes, M. J.; Wulff, W. D. Tetrahedron 2000, 56, 2183-2194.
37. Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344-1346.