A well-defined complex for palladium-catalyzed aerobic oxidation of alcohols: Design, synthesis, and mechanistic considerations

Angewandte Chemie - International Edition

Volumn 42, Issue 32, 2003, Pages 3810-3813

  Jensen, David R ^a   Schultz, Mitchell J ^a   Mueller, Jaime A ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Alcohols; Oxidation; Oxygen; Palladium; Reaction mechanisms

Indexed keywords

CATALYSIS; CRYSTAL STRUCTURE; HYDROGEN BONDS; ISOTOPES; OXIDATION; PALLADIUM; SYNTHESIS (CHEMICAL);

AEROBIC OXIDATION;

ALCOHOLS;

ALCOHOL; PALLADIUM;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; COMPLEX FORMATION; CRYSTAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

AEROBIOSIS; ALCOHOLS; ALLYL COMPOUNDS; BENZYL ALCOHOLS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; THERMODYNAMICS;

EID: 0042865830     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351997     Document Type: Article

References (29)

1. For recent reviews, see a) R. A. Sheldon, I. W. C. E. Arends, G. ten Brink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774;
2. b) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catal. Today 2000, 57, 157.
3. For examples, see a) M. J. Schultz, C. C. Park, M. S. Sigman, Chem. Commun. 2002, 3034;
4. b) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620;
5. c) K. Hallman, C. Moberg, Adv. Synth. Catal. 2001, 343, 260;
6. d) G. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636;
7. e) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 6750;
8. f) K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185.
9. For the use of Pd-catalyzed alcohol oxidation for kinetic resolution, see a) S. K. Mandal, D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Org. Chem. 2003, 68, 4600; b) J. T. Bagdanoff, E. M. Ferreira, B. M. Stoltz, Org. Lett. 2003, 5, 835; c) D. R. Jensen, M. S. Sigman, Org. Lett. 2003, 5, 63; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; e) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475.
10. For the use of Pd-catalyzed alcohol oxidation for kinetic resolution, see a) S. K. Mandal, D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Org. Chem. 2003, 68, 4600; b) J. T. Bagdanoff, E. M. Ferreira, B. M. Stoltz, Org. Lett. 2003, 5, 835; c) D. R. Jensen, M. S. Sigman, Org. Lett. 2003, 5, 63; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; e) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475.
11. For the use of Pd-catalyzed alcohol oxidation for kinetic resolution, see a) S. K. Mandal, D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Org. Chem. 2003, 68, 4600; b) J. T. Bagdanoff, E. M. Ferreira, B. M. Stoltz, Org. Lett. 2003, 5, 835; c) D. R. Jensen, M. S. Sigman, Org. Lett. 2003, 5, 63; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; e) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475.
12. For the use of Pd-catalyzed alcohol oxidation for kinetic resolution, see a) S. K. Mandal, D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Org. Chem. 2003, 68, 4600; b) J. T. Bagdanoff, E. M. Ferreira, B. M. Stoltz, Org. Lett. 2003, 5, 835; c) D. R. Jensen, M. S. Sigman, Org. Lett. 2003, 5, 63; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; e) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475.
13. For the use of Pd-catalyzed alcohol oxidation for kinetic resolution, see a) S. K. Mandal, D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Org. Chem. 2003, 68, 4600; b) J. T. Bagdanoff, E. M. Ferreira, B. M. Stoltz, Org. Lett. 2003, 5, 835; c) D. R. Jensen, M. S. Sigman, Org. Lett. 2003, 5, 63; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725; e) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475.
14. For mechanistic studies, see a) J. A. Mueller, M. S. Sigman, J. Am. Chem. Soc. 2003, 125, 7005;
15. b) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202;
16. c) B. A. Steinhoff, S. S. Stahl, Org. Lett. 2002, 4, 4179;
17. d) B. A. Steinhoff, S. R. Fix, S. S. Stahl, J. Am. Chem. Soc. 2002, 124, 766;
18. e) G. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355;
19. f) S. S. Stahl, J. L. Thorman, R. C. Nelson, M. A. Kozee, J. Am. Chem. Soc. 2001, 123, 7188.
20. 2O at 100°C and 30 atm, the oxidation precedes by dissociation of anionic ligands.
21. For a review of NHC ligands, see W. A. Hermann, Angew. Chem. 2002, 114, 1342; Angew. Chem. Int. Ed. 2002, 41, 1290.
22. For a review of NHC ligands, see W. A. Hermann, Angew. Chem. 2002, 114, 1342; Angew. Chem. Int. Ed. 2002, 41, 1290.
23. For evidence of acetate acting as a base, see ref. [4b].
24. -3.
25. For a homogeneous Pd catalyst using air, see ref. [2c]. For a heterogeneous Pd catalyst using air, see ref. [2b].
26. 1H NMR spectra for the complex formed in situ and after recrystallization.
27. The hydrogen atoms of the water molecule were located and found to be within the van der Waal radii of the acetate and the water. See Supporting Information for details.
28. See ref. [4b,c,e] and G. Noronha, P. M. Henry, J. Mol. Catal. A 1997, 120, 75.
29. II-hydride species under acidic conditions, see C. Amatore, A. Jutand, G. Meyer, I. Carelli, I. Chiarotto, Eur. J. Inorg. Chem. 2000, 1855.