Activator-free olefin oligomerization and isomerization reactions catalyzed by an air- and water-tolerant wacker oxidation intermediate

Angewandte Chemie - International Edition

Volumn 51, Issue 39, 2012, Pages 9822-9824

  Winston, Matthew S ^a   Oblad, Paul F ^a   Labinger, Jay A ^a   Bercaw, John E ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

isomerization; oligomerization; oxidation; palladium; thermodynamics

Indexed keywords

C-H ACTIVATION; ISOMERIZATION CATALYSTS; ISOMERIZATION REACTION; OLEFIN OLIGOMERIZATION; WACKER OXIDATION;

ACTIVATION ANALYSIS; ISOMERIZATION; ISOMERS; KETONES; OLIGOMERIZATION; OLIGOMERS; OXIDATION; PALLADIUM; REACTION INTERMEDIATES; THERMODYNAMICS;

OLEFINS;

EID: 84866496002     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206215     Document Type: Article

References (25)

1. W. Keim, F. H. Kowaldt, R. Goddard, C. Krüger, Angew. Chem. 1978, 90, 493-493
2. Angew. Chem. Int. Ed. Engl. 1978, 17, 466-467
3. W. Keim, Angew. Chem. 1990, 102, 251-260
4. Angew. Chem. Int. Ed. Engl. 1990, 29, 235-244.
5. F. Speiser, P. Braunstein, L. Saussine, Acc. Chem. Res. 2005, 38, 784-793.
6. L. K. Johnson, C. M. Killian, M. B. Brookhart, J. Am. Chem. Soc. 1995, 117, 6414-6415
7. S. Svejda, M. B. Brookhart, Organometallics 1999, 18, 65-74
8. S. D. Ittel, L. K. Johnson, M. Brookhart, Chem. Rev. 2000, 100, 1169-1204
9. D. P. Gates, S. A. Svejda, E. Oñate, C. M. Killian, L. K. Johnson, P. S. White, M. Brookhart, Macromolecules 2000, 33, 2320-2334.
10. B. L. Small, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 7143-7144.
11. Synthesized in one step from commercially available 3,5-di-tert- butylaniline and 2,3-butanedione. See:, H. A. Zhong, J. A. Labinger, J. E. Bercaw, J. Am. Chem. Soc. 2002, 124, 1378-1399.
12. L. J. Ackerman, J. P. Sadighi, D. M. Kurtz, J. A. Labinger, J. E. Bercaw, Organometallics 2003, 22, 3884-3890.
13. T. J. Williams, A. J. M. Caffyn, N. Hazari, P. F. Oblad, J. A. Labinger, J. E. Bercaw, J. Am. Chem. Soc. 2008, 130, 2418-2419
14. J. E. Bercaw, N. Hazari, J. A. Labinger, P. F. Oblad, Angew. Chem. 2008, 120, 10089-10091
15. Angew. Chem. Int. Ed. 2008, 47, 9941-9943.
16. D. R. Stull, E. F. Westrum, Jr., G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York, 1969.
17. J. D. Cox, G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, London, 1970.
18. F. D. Rossini, Chemical Thermodynamics, Wiley, New York, 1950.
19. J. E. Kilpatrick, J. P. Prosen, K. S. Pitzer, F. D. Rossini, J. Res. Natl. Bur. Stand. 1946, 36, 559-612.
20. M. L. Kirova, D. B. Dahl, W. G. Lloyd, J. Mol. Catal. 1994, 88, 301-310
21. D. B. Dahl, C. Davies, R. Hyden, M. L. Kirova, W. G. Lloyd, J. Mol. Catal. A 1997, 123, 91-101.
22. G. A. Foulds, A. M. A. Bennett, D. A. Thornton, S. J. Brown, L. M. Clutterbuck, C. Hinton, G. B. Humphreys, A. F. Masters, Polyhedron 1992, 11, 1285.
23. T. A. Manuel, J. Org. Chem. 1962, 27, 3941-3945.
24. J. A. Keith, R. J. Nielsen, J. Oxgaard, W. A. Goddard, J. Am. Chem. Soc. 2007, 129, 12342-12343.
25. J. Feldman, S. J. McLain, A. Parthasarathy, W. J. Marshall, J. C. Calabrese, S. D. Arthur, Organometallics 1997, 16, 1514-1516.