Critical Role of the Coordination Environment of Palladium Dichloride on the Course of Its Reaction with Secondary Benzylic Alcohols: Selective Oxidation or Etherification Catalysts

Organometallics

Volumn 19, Issue 7, 2000, Pages 1434-1437

  Bouquillon, Sandrine ^a   Hénin, Françoise ^a   Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001153406     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990961q     Document Type: Article

References (59)

1. 10)ammonium chloride.
2. (a) Aït-Mohand, S.; Hénin, F.; Muzart, J. Tetrahedron Lett. 1995, 36, 2473.
3. (b) Aït-Mohand, S.; Muzart, J. J. Mol. Catal. 1998, 129, 135.
4. (c) Aït-Mohand, S. Ph.D. Thesis, University of Reims Champagne-Ardenne, 1997.
5. 2a,c
6. Bouquillon, S.; du Moulinet d'Hardemare, A.; Averbuch-Pouchot, M.-Th.; Hénin, F.; Muzart, J. Polyhedron 1999, 18, 3511.
7. 2 exhibit an oligomeric structure: (a) Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 1, p 43. (b) Hartley, F. R. The Chemistry of Platinum and Palladium; J. Wiley: New York, 1973; p 470.
8. 2 exhibit an oligomeric structure: (a) Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 1, p 43. (b) Hartley, F. R. The Chemistry of Platinum and Palladium; J. Wiley: New York, 1973; p 470.
9. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
10. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
11. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
12. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
13. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
14. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
15. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
16. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
17. The more or less effective palladium-catalyzed oxidation of alcohols with oxygen as terminal oxidant has been reported: (a) Lloyd, W. G. J. Org. Chem. 1967, 32, 2816. (b) Blackburn, T. F.; Schwartz, J. S. Chem. Commun. 1977, 157. (c) Gomez-Bengoa, E.; Noheda, P.; Echavaren, A. E. Tetrahedron Lett. 1994, 35, 7097. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023. (f) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011. (g) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (h) Nagata, H.; Ogasawa, K. Tetrahedron Lett. 1999, 40, 6617. (i) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
18. Indeed, we have observed that some experiments reported in the present paper were very air sensitive.
19. Bouquillon, S.; Aït-Mohand, S.; Muzart, J. Eur. J. Org. Chem. 1998, 2599.
20. (a) Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286.
21. (b) Almeida, M. L. S.; Beller, M.; Wang, G.-Z.; Bäckvall, J.-E. Chem. Eur. J. 1986, 48, 1533.
22. (a) Trost, B. M.; Masuyama, Y. Tetrahedron Lett. 1984, 25, 173.
23. See also: (b) Schwarz, I.; Braun, M. Chem. Eur. J. 1999, 5, 2300.
24. Zhao, F.; Bhanage, B. M.; Shirai, M.; Arai, M. J. Mol. Catal. A: Chem. 1999, 142, 383.
25. Aït-Mohand, S.; Lunak, S.; Muzart, J. Chem. Ber. / Recl. 1997, 130, 1655.
26. Salehi, P.; Iranpoor, N.; Behbahani, F. K. Tetrahedron 1998, 54, 943.
27. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
28. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
29. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
30. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
31. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
32. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
33. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
34. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet-Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
35. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
36. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
37. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
38. For metal-catalyzed reactions carried out in BTF, see: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531. (b) Curran, D. P.; Hoshim, M. J. Org. Chem. 1996, 61, 6480. (c) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (d) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Nishikido, J.; Nakajima, H.; Saeki, T.; Ishii, A.; Mikami, K. Synlett 1998, 1347. (f) Ravikumar, K. S.; Bégué, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (h) Ravikumar, K. S.; Barbier, F.; Bégué, J.-P.; Bonnet- Delpon, D. Tetrahedron 1998, 54, 7457. (i) Olofsson, K.; Kim, S.-Y.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1999, 64, 4539. (j) De Campo, F.; Lastécouères, D.; Vincent, J.-M.; Verlhac, J.-B. J. Org. Chem. 1999, 64, 4969. (k) Delaval, N.; Bouquillon, S.; Hénin, F.; Muzart J. J. Chem. Res., Synop. 1999, 286. (l) Takezawa, E.; Sakaguchi, S.; Ishii, Y. Org. Lett. 1999, 1, 713.
39. 16
40. (a) Sen, A.; Lai, T.-W. J. Am. Chem. Soc. 1981, 103, 4627.
41. (b) Sen, A.; Lai, T.-W. Organometallics 1983, 2, 1059.
42. (a) Lipshutz, B. H.; Pollart, D.; Monforte, J.; Kotsuki, H. Tetrahedron Lett. 1985, 26, 705.
43. (b) Tenaglia, A.; Kammerer, F. Synlett 1996, 576.
44. 4
45. 2 was used as catalyst.
46. 2 as catalyst for the oxidation of alcohols under phase transfer conditions has been reported: Choudary, B. M.; Reddy, N. P.; Kantam, M. L.; Jamil, Z. Tetrahedron Lett. 1985, 26, 6257.
47. Even with Pd(0), it has been argued that the coordination of chloride ions to palladium makes it more nucleophilic: Larock, R. C. J. Organomet. Chem. 1999, 576, 111.
48. 4 Thus, we consider that in run 1 this latter salt is the active catalyst.
49. 3.
50. 25 As remarked by a referee, eq 3 is almost certainly an oversimplification.
51. (a) Henry, P. M. Palladium Catalyzed Oxidation of Hydrocarbons; D. Reidel: Dordrecht, 1979; pp 11-16.
52. (b) Sarhan, J. K. K.; Foong Murray, S.-W.; Asfour, H. M.; Green, M.; Wing, R. M.; Parra-Haake, M. Inorg. Chem. 1986, 25, 243.
53. For recent work on catalytic symmetrical etherifications, see: Bagnell, L.; Cablewski, T.; Strauss, C. R. Chem. Commun. 1999, 283.
54. (a) Balsells, R. A.; Frasca, A. R. Tetrahedron 1982, 38, 2525.
55. (b) Johnson, A. L. J. Org. Chem. 1982, 47, 5220.
56. (c) Liotta, L.; Gamen, B. Tetrahedron Lett. 1989, 30, 4759.
57. (d) Zhu, Z.; Espenson, J. H. J. Org. Chem. 1996, 61, 324.
58. (e) Malkar, N. B.; Kumar, V. G. Synth. Commun. 1998, 28, 971.
59. Bellesia, F.; Ghelfi, F.; Pagoni, U. M.; Pinetti, A. Gazz. Chim. Ital. 1992, 122, 437.