Iridacyclopentadiene reactions with terminal alkynes: Tandem cycloaromatization and orthometalation

Organometallics

Volumn 20, Issue 17, 2001, Pages 3710-3717

  O'Connor, Joseph M ^a   Closson, Adam ^a   Hiibner, Kristin ^a   Merwin, Richard ^a   Gantzel, Peter ^a   Roddick, Dean M ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF WYOMING   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNES; BENZENETETRACARBOXYLATE; CYCLOAROMATIZATION; DEMETALATION; ETHYL ETHYNYL ETHER; ETHYNE; IRIDACYCLOPENTADIENE; METHYL PROPAGYL ETHER; ORTHOMETALATION; SILVER TETRAFLUOROBORATE;

ADDITION REACTIONS; ALCOHOLS; AROMATIC COMPOUNDS; CARBON MONOXIDE; COMPLEXATION; CRYSTAL STRUCTURE; ESTERIFICATION; ESTERS; FLUORINE COMPOUNDS; HYDROCHLORIC ACID; SUBSTRATES; X RAY CRYSTALLOGRAPHY;

IRIDIUM COMPOUNDS;

EID: 0035921535     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0102450     Document Type: Article

References (57)

1. For leading references to metal-mediated alkyne cyclotrimerization see: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549.
2. (b) Ozerov, O. V.; Ladipo, F. T.; Partick, B. O. J. Am. Chem. Soc. 1999, 121, 7941.
3. (c) Hecht, S.; Fréchet, M. J. J. Am. Chem. Soc. 1999, 121, 4084.
4. (d) Sherrill, A. B.; Lusvardi, V. S.; Barteau, M. A. Langmuir 1999, 15, 7615.
5. (e) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827.
6. (f) Sigman, M. S.; Fatland, A. W.; Eaton, B. E. J. Am. Chem. Soc. 1998, 120, 5130.
7. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
8. (h) Bönnemann, H. Angew. Chem. 1985, 97, 264.
9. Diercks, R.; Eaton, B. E.; Gurtzgen, S.; Jalisatgi, S.; Matzger, A. J.; Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1998, 120, 8247.
10. (b) Baxter, R. J.; Knox, G. R.; Pauson, P. L.; Spicer, M. D. Organometallics 1999, 18, 197.
11. (c) Takahashi, T.; Tsai, R. Y.; Li, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1999, 121, 11093.
12. (d) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672.
13. (e) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1968, 7, 1298.
14. Other mechanistic possibilities, most notably the initial formation of a vinylidene ligand followed by addition of alkyne across the iridium-carbon double bond, are potentially viable [2+2+1] routes toward fulveness; see ref 6.
15. O'Connor, J. M.; Hiibner, K.; Merwin, R.; Gantzel, P.; Rheingold, A. L.; Fong, B. S. J. Am. Chem. Soc. 1997, 119, 3631.
16. For an early-metal metallacyclopentadiene to fulvene cyclization see: Johnson, E. S.; Balaich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086-11087.
17. For other [2+2+1] alkyne cyclotrimerizations see: (a) Moran, G.; Green, M.; Orpen, A. G. J. Organomet. Chem. 1983, 250, C15.
18. (b) Moreto, J.; Maruya, K.; Bailey, P. M.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1982, 1341.
19. (c) Kim, H. J.; Choi, N. S.; Lee, S. W. J. Organomet. Chem. 2000, 616, 67.
20. (d) Chuckhadzhyan, G. A.; Abramyan, Zh. Igevorkyan, G. A. Zh. Obshch. Khim. 1973, 43, 2012.
21. (e) Chukhadzhyan, G. A.; Abramyan, Zh. I.; Tonyan, G. M.; Matosyan, V. A. Zh. Org. Khim. 1974, 10, 1994.
22. (f) Chukhadzhyan, G. A.; Abramyan, Zh. I.; Tonyan, G. M.; Sagradyan, L. I.; Elbakyan, T. S. Zh. Org. Khim. 1981, 17, 1831.
23. O'Connor, J. M.; Pu, L.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 6232.
24. (b) O'Connor, J. M.; Pu, L.; Woolard, S.; Chadha, R. K. J. Am. Chem. Soc. 1990, 112, 6731.
25. (c) O'Connor, J. M.; Hiibner, K.; Rheingold, A. L. J. Chem. Soc., Chem. Commun. 1995, 1209.
26. (d) O'Connor, J. M.; Hiibner, K.; Merwin, R.; Pu, L.; Rheingold, A. L. J. Am. Chem. Soc. 1995, 117, 8861.
27. O'Connor, J. M.; Pu, L.; Chadha, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 543.
28. (b) O'Connor, J. M.; Pu, L. J. Am. Chem. Soc. 1990, 112, 9013.
29. (c) O'Connor, J. M.; Pu, L.; Chadha, R. K. J. Am. Chem. Soc. 1990, 112, 9627.
30. (d) O'Connor, J. M.; Pu, L.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 9663.
31. Mayer, H. A.; Kaska, W. C. Chem. Rev. 1994, 94, 1239.
32. Yamazaki, H.; Hagihara, N. J. Organomet. Chem. 1967, 7, 22.
33. (b) Ville, G.; Vollhardt, K. P. C.; Winter, M. J. J. Am. Chem. Soc. 1981, 103, 5267.
34. O'Connor, J. M.; Hiibner, K.; Closson, A.; Gantzel, P. Organometallics 2001, 20, 1482.
35. Arpac, E.; Dahlenburg, L. Chem. Ber. 1985, 118, 3188.
36. For details of the X-ray crystallographic analysis see Supporting Information.
37. Stephan, C.; Munz, C.; tom Dieck, H. J. Organomet. Chem. 1993, 452, 223.
38. For a detailed mechanistic study on reductive elimination of aromatics from Ir(III) aryl-hydride complexes see: Rosini, G. P.; Wang, K.; Patel, B.; Goldman, A. S. Inorg. Chim. Acta 1998. 270, 537.
39. Suzuki, H.; Itoh, K.; Ishii, Y.; Simon, K.; Ibers, J. A. J. Am. Chem. Soc. 1976, 98, 8494.
40. Barbaro, P.; Bianchini, C.; Meli, A.; Peruzzini, M.; Vacca, A.; Vizza, F. Organometallics 1991, 10, 2227.
41. O'Connor, J. M.; Closson, A., unpublished observation.
42. Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M. L.; Eisenstein, O.; Jackson, S. A.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
43. (b) Bianchini, C.; Caulton, K. G.; Chardon, C.; Eisenstein, O.; Folting, K.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Rauscher, D. J.; Streib, W. E.; Vizza, F. J. Am. Chem. Soc. 1991, 113, 5127.
44. Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
45. (b) Alaimo, P. J.; Arndtsen, B. A.; Bergman, R. G. Organometallics 2000, 19, 2130.
46. (c) Fuchen, L.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
47. (d) Aoki, T.; Crabtree, R. H. Organometallics 1993, 12, 294.
48. Shu, A. Y. L.; Chen, W.; Heys, J. R. J. Organomet. Chem. 1996, 524, 87.
49. Kingston, L. P.; Lockley, W. J. S.; Mather, A. N.; Spink, E.; Thompson, S. P.; Wilkinson, D. J. Tetrahedron Lett. 2000, 41, 2705.
50. Ainscough, E. W.; Robinson, S. D.; Levison, J. J. J. Chem. Soc. (A) 1971, 3413.
51. (b) Deuton, K.; Dahlenburg, L. Transition Met. Chem. 1980, 5, 222.
52. (c) Dahlenburg, L. J. Organomet. Chem. 1983, 251, 215.
53. (d) Aizenberg, M.; Milstein, D. Organometallics 1996, 15, 3317.
54. (e) Cooper, A. C.; Huffman, J. C.; Caulton, K. G. Organometallics 1997, 16, 1974.
55. Bianchini, C.; Barbaro, P.; Meli, A.; Peruzzini, M.; Vacca, A.; Vizza, F. Organometallics 1993, 12, 2505.
56. Klei, S. R.; Tilley, T. D.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 1816.
57. (b) Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1998, 120, 6169.