Direct Synthesis of Cyclic Ketals of Acetophenones by Palladium-Catalyzed Arylation of Hydroxyalkyl Vinyl Ethers

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7863-7868

  Larhed, Mats ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542605386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971454q     Document Type: Article

References (71)

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9. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345-363. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London 1985; pp 276-290. (c) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; vol. 4, pp 833-863. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (f) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-168. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S. Ed.; JAI Press Inc: Greenwich, CT, 1996; vol. 5, pp 153-260. For Heck arylation of heteroatom-substituted double bonds see: (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433-1445.
10. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345-363. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London 1985; pp 276-290. (c) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; vol. 4, pp 833-863. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (f) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-168. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S. Ed.; JAI Press Inc: Greenwich, CT, 1996; vol. 5, pp 153-260. For Heck arylation of heteroatom-substituted double bonds see: (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433-1445.
11. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345-363. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London 1985; pp 276-290. (c) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; vol. 4, pp 833-863. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (f) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-168. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S. Ed.; JAI Press Inc: Greenwich, CT, 1996; vol. 5, pp 153-260. For Heck arylation of heteroatom-substituted double bonds see: (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433-1445.
12. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345-363. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London 1985; pp 276-290. (c) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; vol. 4, pp 833-863. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (f) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-168. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S. Ed.; JAI Press Inc: Greenwich, CT, 1996; vol. 5, pp 153-260. For Heck arylation of heteroatom-substituted double bonds see: (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433-1445.
13. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345-363. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London 1985; pp 276-290. (c) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; vol. 4, pp 833-863. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (f) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-168. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S. Ed.; JAI Press Inc: Greenwich, CT, 1996; vol. 5, pp 153-260. For Heck arylation of heteroatom-substituted double bonds see: (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433-1445.
14. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345-363. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London 1985; pp 276-290. (c) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; vol. 4, pp 833-863. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (f) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-168. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S. Ed.; JAI Press Inc: Greenwich, CT, 1996; vol. 5, pp 153-260. For Heck arylation of heteroatom-substituted double bonds see: (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433-1445.
15. For internal arylation of acyclic vinyl ethers see: (a) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654-3655. (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481-1486. For an earlier report of preferential formation of internal arylation products see: (c) Hallberg, A.; Westfelt, L.; Holm, B. J. Org. Chem. 1981, 46, 5414-5415.
16. For internal arylation of acyclic vinyl ethers see: (a) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654-3655. (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481-1486. For an earlier report of preferential formation of internal arylation products see: (c) Hallberg, A.; Westfelt, L.; Holm, B. J. Org. Chem. 1981, 46, 5414-5415.
17. For internal arylation of acyclic vinyl ethers see: (a) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654-3655. (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481-1486. For an earlier report of preferential formation of internal arylation products see: (c) Hallberg, A.; Westfelt, L.; Holm, B. J. Org. Chem. 1981, 46, 5414-5415.
18. For a somewhat related transformation of organic halides or organic triflates to cyclic hemiacetals see: (a) Mandai, T.; Hasegawa, S.; Fujimoto, T.; Kawada, M.; Nokami, J.; Tsuji, J. Synlett 1990, 85-86. (b) Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Tetrahedron 1991, 47, 1525-1540.
19. For a somewhat related transformation of organic halides or organic triflates to cyclic hemiacetals see: (a) Mandai, T.; Hasegawa, S.; Fujimoto, T.; Kawada, M.; Nokami, J.; Tsuji, J. Synlett 1990, 85-86. (b) Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Tetrahedron 1991, 47, 1525-1540.
20. No terminal β-products were detected (GC-MS) in DPPP-controlled arylations of hydroxyalkyl vinyl ethers.
21. In this case, only a small amount of product 3e was formed (18% isolated yield after 120 h at 80°C).
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24. We are aware of only one additional methodology for selective ketalization of ketones in the presence of aldehydes (reversed chemoselectivity). (a) Kim, S.; Kim, Y. G.; Kim, D. Tetrahedron Lett. 1992, 33, 2565-2566. For a recent example of a selective acetalization of an aromatic aldehyde in the presence of a ketone see: Tateiwa, J.; Horiuchi, H.; Uemura, S. J. Org. Chem. 1995, 60, 4039-4043.
25. We are aware of only one additional methodology for selective ketalization of ketones in the presence of aldehydes (reversed chemoselectivity). (a) Kim, S.; Kim, Y. G.; Kim, D. Tetrahedron Lett. 1992, 33, 2565-2566. For a recent example of a selective acetalization of an aromatic aldehyde in the presence of a ketone see: Tateiwa, J.; Horiuchi, H.; Uemura, S. J. Org. Chem. 1995, 60, 4039-4043.
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36. Leading references for use of thallium(I) additives. (a) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687-690. (b) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R.; Fiorani, T. J. Org. Chem. 1991, 56, 261-263. Sonesson, C.; Larhed, M.; Nyqvist, C.; Hallberg, A. J. Org. Chem. 1996, 61, 4756-4763. Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147-7155. See also ref 5b.
37. Leading references for use of thallium(I) additives. (a) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687-690. (b) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R.; Fiorani, T. J. Org. Chem. 1991, 56, 261-263. Sonesson, C.; Larhed, M.; Nyqvist, C.; Hallberg, A. J. Org. Chem. 1996, 61, 4756-4763. Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147-7155. See also ref 5b.
38. Leading references for use of thallium(I) additives. (a) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687-690. (b) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R.; Fiorani, T. J. Org. Chem. 1991, 56, 261-263. Sonesson, C.; Larhed, M.; Nyqvist, C.; Hallberg, A. J. Org. Chem. 1996, 61, 4756-4763. Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147-7155. See also ref 5b.
39. Leading references for use of thallium(I) additives. (a) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687-690. (b) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R.; Fiorani, T. J. Org. Chem. 1991, 56, 261-263. Sonesson, C.; Larhed, M.; Nyqvist, C.; Hallberg, A. J. Org. Chem. 1996, 61, 4756-4763. Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147-7155. See also ref 5b.
40. For beneficial effects of silver additives see: (a) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. (b) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 57, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954.
41. For beneficial effects of silver additives see: (a) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. (b) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 57, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954.
42. For beneficial effects of silver additives see: (a) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. (b) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 57, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954.
43. For beneficial effects of silver additives see: (a) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. (b) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 57, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954.
44. For beneficial effects of silver additives see: (a) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. (b) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 57, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954.
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48. For examples of Pd(II)-oxygen coordination in Heck reactions see: (a) Bernocchi, E.; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron. Lett. 1992, 33, 3073-3076. (b) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133-1136. Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287-6290. Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J. J. Org. Chem. 1996, 61, 2604-2605. See also ref 6b.
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50. For examples of Pd(II)-oxygen coordination in Heck reactions see: (a) Bernocchi, E.; Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron. Lett. 1992, 33, 3073-3076. (b) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133-1136. Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287-6290. Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J. J. Org. Chem. 1996, 61, 2604-2605. See also ref 6b.
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