Palladium-catalyzed, carboxylic acid-assisted allylic substitution of carbon nucleophiles with allyl alcohols as allylating agents in water

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3241-3244

  Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ADAMANTANECARBOXYLIC ACID; ALCOHOL DERIVATIVE; CARBON; CARBOXYLIC ACID DERIVATIVE; PALLADIUM; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; SUBSTITUTION REACTION; SUSPENSION;

EID: 0141632769     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035126q     Document Type: Article

References (40)

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24. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
25. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
26. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
27. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
28. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
29. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
30. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
31. For palladium-catalyzed allylic substitution in water, see: (a) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843. (b) Uozumi, Y. ; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (d) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (e) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115. (f) Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461. (g) Hashizume, T.; Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2000, 65, 5197. Palladium-catalyzed allylic amination of 1,1-dimethylallyl alcohol in water was observed: (h) Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803.
32. For examples of the use of Pd catalysts with carboxylic acids, see: (a) Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161. (b) Kadota, I.; Shibuya, A.; Gyoung, Y. S.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 10262.
33. For examples of the use of Pd catalysts with carboxylic acids, see: (a) Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161. (b) Kadota, I.; Shibuya, A.; Gyoung, Y. S.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 10262.
34. DBSA has been successfully used for acid-catalyzed reactions in water: (a) Manabe, K.; Mori, Y.; Kobayashi, S. Tetrahedron 2001, 57, 2537. (b) Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971.
35. DBSA has been successfully used for acid-catalyzed reactions in water: (a) Manabe, K.; Mori, Y.; Kobayashi, S. Tetrahedron 2001, 57, 2537. (b) Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971.
36. 2H in water at 70°C for 10 min without the palladium catalyst gave only a trace amount of 3a. This result indicates that the existence of another, acid-catalyzed pathway in the case of 2b is not likely.
37. 2H in water under reflux conditions for 10 min gave only a trace amount of the corresponding ester, indicating that the ester formation was much slower than the allylic substitution. For the equilibrium positions of ester formation of hydrophobic substrates in water, see ref 7b.
38. Amatore, C.; Jutand, A.; Meyer, G.; Mottier, L. Chem. Eur. J. 1999, 5, 466.
39. In rhodium-catalyzed cross coupling of allyl alcohols with boronic acids, Kabalka et al. discussed the effect of a stoichiometric amount of HF as an additive in a similar manner: Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 893.
40. Giambastiani, G.; Poli, G. J. Org. Chem. 1998, 63, 9608.