Highly active and selective platinum(II)-catalyzed isomerization of allylbenzenes: Efficient access to (E)-anethole and other fragrances via unusual agostic intermediates

Organometallics

Volumn 29, Issue 6, 2010, Pages 1487-1497

  Scarso, Alessandro ^a   Colladon, Marco ^a   Sgarbossa, Paolo ^b   Santo, Claudio ^a   Michelin, Rino A ^b   Strukul, Giorgio ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLBENZENE; ANETHOLE; CATALYTIC MECHANISMS; CATALYTIC SYSTEM; DFT CALCULATION; DIPHOSPHINES; E-ISOMERS; EXPERIMENTAL CONDITIONS; HYDRIDE ELIMINATION; INTERMEDIATE SPECIE; ISOMERIZATION REACTION; KINETIC STUDY; STERIC HINDRANCES; TERMINAL ALKENES;

COORDINATION REACTIONS; ELECTRON TRANSITIONS; ISOMERIZATION; ISOMERS; ODORS; OLEFINS; SULFUR COMPOUNDS;

PLATINUM;

EID: 77949479761     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100033a     Document Type: Article

References (67)

1. van Leeuwen P. W. N. M. Homogeneous Catalysis; Kluwer Academic Publishers: Dordrecht, 2004; pp 101-105.
2. Parshall G. W.; Ittel S. D. Homogeneous Catalysis, 2nd ed.;Wiley: New York, 1992; pp 9-24.
3. Cornils B.; Herrmann W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley: New York, 2002; pp 980-991.
4. (a) Bauer K.; Garbe D.; Surburg H. Common Fragrance and Flavour Materials, 4th ed.;Wiley: New York, 2001; pp 171-226.
5. (b) Kraft P.; Swift K. A. D. Current Topics in Flavour and Frangrance Research; Swift, K. A. D., Ed.; VHCA, Zürich, Switzerland, and Wiley-VCH Veralg GmbH, Weinheim, Germany, 2008.
6. Chapuis, C.; Jacoby, D. Appl. Catal. A 2001, 221, 93-117.
7. Pommer, H.; Nurrenbach, A. Pure Appl. Chem. 1975, 43, 527-552.
8. Inoue, S.-I.; Takaya, H.; Tani, K.; Otsuka, S.; Sato, T.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 4897-4905.
9. Sharma, S. K.; Srivastava, V. K.; Jasra, R. V. J. Mol. Catal. A 2006, 245, 200-209.
10. (a) Kishore, D.; Kannan, S. Green Chem. 2002, 4, 607-610.
11. (b) Srivastava, V. K.; Bajaj, H. C.; Jasra, R. V. Catal. Commun. 2003, 4, 543-548.
12. (c) Kishore, D.; Kannan, S. J. Mol. Catal. A 2004, 223, 225-230.
13. (d) Kishore, D.; Kannan, S. App. Catal. A 2004, 270, 227-235.
14. (e) Kishore, D.; Kannan, S. J. Mol. Catal. A 2006, 244, 83-92.
15. Tuner, M.; Jouanne, J. V.; Brauer, H.-D.; Kelm, H. J. Mol. Catal. 1979, 5 (425), 433-447.
16. (a) Morrill, T. C.; D'Souza, C. A. Organometallics 2003, 22, 1626-1629.
17. (b) Yan,Y.; Zhang, X.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 16058-16061.
18. (c) Tan, K. L.; Bergman, R. G.; Ellman, J. J. A. Am. Chem. Soc. 2002, 124, 13964-13965.
19. (a) Schmidt, B. Chem. Commun. 2004, 742-743.
20. (b) Sharma, S. K.; Srivastava, V. K.; Pandya, P. H.; Jasra, R. V. Catal. Commun. 2005, 6, 205-209.
21. (c) Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8, 5481-5484.
22. (d) Courchay, F. C.; Sworen, J. C.; Ghiviriga, I.; Abboud, K. A.; Wagener,K.B. Organometallics 2006, 25, 6074-6086.
23. (e)Yue, C. J.; Liu,Y.; He, R. J. Mol. Catal. A 2006, 259, 17-22.
24. (f) Krompiec, S.; Kuźnik, N.; Urbala, M.; Rzepa, J. J. Mol. Catal. A 2006, 248, 198-209.
25. (g) Donohoe, T. J.; O'Riordan, T. J. C.; Rosa, C. P. Angew. Chem. 2009, 121, 1032-1035.
26. Angew. Chem., Int. Ed., 2009, 48, 1014-1017;
27. (h) Erdogan, G.; Grotjahn, D. B. J. Am. Chem. Soc. 2009, 131, 10354-10355.
28. Baxendale, I. R.; Lee, A.-L.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 2002, 1850-1857.
29. Jennerjahn, R.; Piras, I.; Jackstell, R.; Franke, R.; Wiese, K.-D.; Beller, M. Chem.;Eur. J. 2009, 15, 6383-6388.
30. Kim, I. S.; Dong, G. R.; Jung, Y. H. J. Org. Chem. 2007, 72, 5424-5426.
31. Zhang, J.; Gao, H.; Ke, Z.; Bao, F.; Zhu, F.; Wu, Q. J. Mol. Catal. A 2005, 231, 27-34.
32. (a) Colladon, M.; Scarso, A.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. J. Am. Chem. Soc. 2006, 128, 14006-14007.
33. (b) Colladon, M.; Scarso, A.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. J. Am. Chem. Soc. 2007, 129, 7680-7689.
34. (c) Pizzo, E.; Sgarbossa, P.; Scarso, A.; Michelin, R. A.; Strukul, G. Organometallics 2006, 25, 3056-3062.
35. Brett Runge, M.; Mwangi, M. T.; Bowden, N. B. J. Organomet. Chem. 2006, 691, 5278-5288.
36. Grimme, S.; Steinmetz, M.; Korth, M. J. Org. Chem. 2007, 72, 2118-2126.
37. Sivaramakrishna, A.; Su, H.; Moss, J. R. Organometallics 2007, 26, 5786-5790.
38. Pt(II)-catalyzed 1-hexene isomerization as side reaction: Karshtedt, D.; Bell, A. T.; Don Tilley, T. J. Am. Chem. Soc. 2005, 127, 12640-12646.
39. (a) Carr, N.; Dunne. B. J.: Mole, L.; Orpen, A. G.: Spencer, J. L. J. Chem. Soc. Dalton Trans. 1991, 863-871.
40. (b)Carr, N.; Mole, L.; Orpen, A. G.; Spencer, J. L. J. Chem. Soc., Dalton Trans. 1992, 2653-2662.
41. (c) Spencer, J. L.; Mhinzi, G. S. J. Chem. Soc., Dalton Trans. 1995, 3819-3824.
42. Mullen, C. A.; Gagne, M. R. J. Am. Chem. Soc. 2007, 129, 11880-11881.
43. Dierkes, P.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans 1999, 1519-1529.
44. Mole, L.; Spencer, J. L.; Carr, N.; Orpen, A. G. Organometallics 1991, 10, 49-52.
45. (a) Crabtree R. H. The Organometallic Chemistry of the Transition Metals; John Wiley & Sons: New York, 1988.
46. (b) Coliman J. P.; Hegedus L. S.; Norton J. T.; Finke R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
47. Creve, S.; Oevering, H.; Coussens, B. B. Organomettallics 1999, 18, 1967-1978.
48. Tempel, D. J.; Brookhart, M. Organometallics 1998, 17, 2290-2296.
49. (a) Sakakura, T. J. Organomet. Chem. 1984, 267, 171.
50. (b) Abatjoglou, A. G.; Billig, E.; Bryant, D. R. Organometallics 1984, 3, 923.
51. Lein, M. Coord. Chem. Rev. 2009, 253, 625-634.
52. Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276-2277.
53. (a) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 122, 9870-9871.
54. (b) Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177-8186.
55. Clark, H. C.; Manzer, L. E. J. Oregnomet. Chem. 1973, 59, 411-428.
56. Eaborn, C.; Odell, K. J.; Pidcock, A. J., Chem. Soc., Dalton Trans 1978, 357-368.
57. Romeo, R.; D'Amico, G. Organometallics 2006, 25, 3435-3446.
58. Zanardo, A.; Michelin, R. A.; Pinna, F.; Strukul, G. Inorg. Chem. 1989, 28, 1648-1653.
59. Al-Fawaz, A.; Aldridge, S.; Coombs, D. L.; Dickinson, A. A.; Willock, D. J.; Ooi, L.-L.; Light, M. E.; Coles, S. J.; Hursthouse,M. B. J. Chem. Soc., Dalton Trans. 2004, 4030-4037.
60. Casado, A. L.; Espinet, P.; Gallego, A. M.; Mart́nez-Ilarduya, J. M. Chem. Commun. 2001, 339-340.
61. Gavagnin, R.; Cataldo, M.; Pinna, F.; Strukul, G. Organometallics 1998, 17, 661-667.
62. (a) te Velde, G.; Bickelhaupt, F. M.; van Gisbergen, S. J. A.; Fonseca Guerra, C.; Baerends, E. J.; Snijders, J. G.; Ziegler, T. Chemistry with ADF. J. Comput. Chem. 2001, 22, 931-967.
63. (b) Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391.
64. (c) ADF2007.01, SCM, Theoretical Chemistry; Vrije Universiteit: Amsterdam, The Netherlands, http://www.scm.com.
65. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
66. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
67. Van Lenthe, E.; Baerends, E. J.; Snijders, J. G. J. Chem. Phys. 1994, 101, 9783.