Functionalization of Benzylic Carbon-Hydrogen Bonds. Mechanism and Scope of the Catalytic Synthesis of Indoles with [Ru(dmpe)2]

Organometallics

Volumn 13, Issue 1, 1994, Pages 385-396

  Hsu, Grace C ^a   Kosar, Walter P ^a   Jones, William D ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; REACTION KINETICS; RUTHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

BENZYLIC CARBON; FUNCTIONALIZATION; HYDROGEN BONDS; INDOLES;

ORGANOMETALLICS;

EID: 0027969825     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00013a056     Document Type: Article

References (32)

1. Houlihan, W. J. Heterocyclic Compounds: Indoles—Part 1; John Wiley & Sons, Inc.: New York, 1970.
2. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
3. Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988,27,1113-1226.
4. Lukehart, C. M. Fundamental Transition Metal Organometallic Chemistry; Brooks Cole Publishing Co.: Monterey, CA, 1985.
5. Davis, S. D. Organotransition Metal Chemistry: Applications to Organic Synthesis; Pergamon Press: Oxford, U.K., 1982.
6. Powell. Principles of Organometallic Chemistry; Chapman & Hall: London, 1988.
7. Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem. Soc. 1976, 98, 2674-2676.
8. Kametani, T.; Takahashi, K.; Ihara, M.; Fukumoto, K. Heterocycles 1975, 3, 691-695.
9. Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S.; Demartin, F. J. Chem. Soc., Chem. Commun. 1986, 784-786.
10. Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986,108, 5640-5641.
11. Hall, C.; Jones, W. D.; Mawby, R. J.; Osman, R.; Pertuz, R. N.; Whittlesey, M. K. J. Am. Chem. Soc. 1992, 114, 7425-7435.
12. Jones, W. D.; Kosar, W. P. Organometallics 1986,5,1823-1829.
13. Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1986, 108, 4814-4819 and references therein.
14. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. 5, pp 1060-1063.
15. Ito, Y.; Kobayasshi, K.; Seko, N.; Saegusa, T. Bull. Chem. Soc. Jpn. 1984, 57, 73-84.
16. Bergman, R. G.; Walsh, P. J.; Hollander, F. J. J. Am. Chem. Soc. 1988, 110, 8729-8733.
17. Rothwell, I. P.; Hill, J. E.; Profilet, R. D.; Fanwick, P. E. Angew. Chem., Int. Ed. Engl. 1990, 29, 664-665.
18. Bercaw, J. E.; Hillhouse, G. L. J. Am. Chem. Soc. 1984,106,5472-5478.
19. Roundhill, D. M.; Hedden, D.; Fultz, W. C.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 6738-6744.
20. Roundhill, D. M.; Hedden, D. Inorg. Chem. 1986, 25, 9-15.
21. Roundhill, D. M.; Hedden, D.; Park, S. Organometallics 1986,5,2151-2152.
22. Roundhill, D. M.; Rauchfuss, T. B. J. Am. Chem. Soc. 1974,96,3098-3105.
23. Roundhill, D. M. Inorg. Chem. 1970, 9, 254-258.
24. Merola, J. S.; Ladipo, F. T. Inorg. Chem. 1990, 29, 4172-4173.
25. Dong, L. Doctoral Dissertation, University of Rochester, 1991.
26. Landis, C. R.; Schaad, D. R. J. Am. Chem. Soc. 1990,112,1628-1629.
27. Bryndza, H. E.; Fultz, W. C.; Tam, W. Organometallics 1985, 4, 939-940.
28. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988,110,6738-6744.
29. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 971-973.
30. Marks, T. J.; Gagne, M. R. J. Am. Chem. Soc. 1988, 111, 4108-4109.
31. Chatt, J.; Davidson, J. M. J. Chem. Soc. 1965, 843-855.
32. Cromer, D. T.; Waber, J. T. International Tables for X-Ray Crystallography; The Kynoch Press: Birminghan, England, 1974; Vol. IV, Tables 2.2B and 2.3.1.