An unusual dehalogenation in the Suzuki coupling of 4-bromopyrrole-2-carboxylates

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 427-430

  Handy, Scott T ^a   Bregman, Howard ^a   Lewis, Jennifer ^a   Zhang, Xiaolei ^a   Zhang, Yanan ^a  

^a BINGHAMTON UNIVERSITY   (United States)

Author keywords

Dehalogenation; Protecting group; Pyrroles; Suzuki coupling

Indexed keywords

BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; NITROGEN; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DEHALOGENATION; PROTECTION;

LATEOLABRAX JAPONICUS;

EID: 0037433940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02615-1     Document Type: Article

References (24)

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2. Jones R.A., Bean G.P. The Chemistry of Pyrroles. 1977;Academic Press, London.
3. For the first reported isolation of the lamellarins, see: Andersen, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495. For other groups involved in these isolation efforts, see: Rami Reddy M. V.; Faulkner, D. J.; Venkateswarlu, Y.; Rama Rao, M. Tetrahedron 1997, 53, 3457-3466; Urban, S.; Capon, R. J. Aust. J. Chem. 1996, 49, 711-713; Davis, R. A.; Carroll, A. R.; Piersens, G. K.; Quinn, R. J. J. Nat. Prod. 1999, 62, 419-424; Kang, H.; Fenical, W. J. Org. Chem. 1997, 62, 3254-3262 and references cited therein.
4. For the first reported isolation of the lamellarins, see: Andersen, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495. For other groups involved in these isolation efforts, see: Rami Reddy M. V.; Faulkner, D. J.; Venkateswarlu, Y.; Rama Rao, M. Tetrahedron 1997, 53, 3457-3466; Urban, S.; Capon, R. J. Aust. J. Chem. 1996, 49, 711-713; Davis, R. A.; Carroll, A. R.; Piersens, G. K.; Quinn, R. J. J. Nat. Prod. 1999, 62, 419-424; Kang, H.; Fenical, W. J. Org. Chem. 1997, 62, 3254-3262 and references cited therein.
5. For the first reported isolation of the lamellarins, see: Andersen, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495. For other groups involved in these isolation efforts, see: Rami Reddy M. V.; Faulkner, D. J.; Venkateswarlu, Y.; Rama Rao, M. Tetrahedron 1997, 53, 3457-3466; Urban, S.; Capon, R. J. Aust. J. Chem. 1996, 49, 711-713; Davis, R. A.; Carroll, A. R.; Piersens, G. K.; Quinn, R. J. J. Nat. Prod. 1999, 62, 419-424; Kang, H.; Fenical, W. J. Org. Chem. 1997, 62, 3254-3262 and references cited therein.
6. For the first reported isolation of the lamellarins, see: Andersen, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495. For other groups involved in these isolation efforts, see: Rami Reddy M. V.; Faulkner, D. J.; Venkateswarlu, Y.; Rama Rao, M. Tetrahedron 1997, 53, 3457-3466; Urban, S.; Capon, R. J. Aust. J. Chem. 1996, 49, 711-713; Davis, R. A.; Carroll, A. R.; Piersens, G. K.; Quinn, R. J. J. Nat. Prod. 1999, 62, 419-424; Kang, H.; Fenical, W. J. Org. Chem. 1997, 62, 3254-3262 and references cited therein.
7. For the first reported isolation of the lamellarins, see: Andersen, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495. For other groups involved in these isolation efforts, see: Rami Reddy M. V.; Faulkner, D. J.; Venkateswarlu, Y.; Rama Rao, M. Tetrahedron 1997, 53, 3457-3466; Urban, S.; Capon, R. J. Aust. J. Chem. 1996, 49, 711-713; Davis, R. A.; Carroll, A. R.; Piersens, G. K.; Quinn, R. J. J. Nat. Prod. 1999, 62, 419-424; Kang, H.; Fenical, W. J. Org. Chem. 1997, 62, 3254-3262 and references cited therein.
8. For a discussion of dehalogenations in Stille couplings, see: Farina V., Krishnamurthy V., Scott W.J. Organic Reactions. 50:1997;John Wiley & Sons, New York.
9. Banwell M.G., Flynn B.L., Hamel E., Hockless D.C.R. Chem. Commun. 1997;207-208.
10. Wang J., Scott A.I. Tetrahedron Lett. 37:1996;3247-3250.
11. Remarkably few reports provide any details regarding dehalogenations in Suzuki coupling reactions, although a few comment simply that dehalogenation is observed as a secondary product. Two major exceptions are: Haseltine, J.; Wang, D. J. Heterocyclic Chem. 1994, 31, 1637-1639 and Ref. 15.
12. For references to cross-coupling reactions with pyrroles, see Refs. 5, 10, 12, 13, 14, 15 and: Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587-3595; Zhou, X.; Tse, M. K.; Wan, T. S. M.; Chan, K. S. J. Org. Chem. 1996, 61, 3590-3593; Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. J. Org. Chem. 1992, 57, 1653-1656; Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497-1499; Dupont, C.; Guenard, D.; Thal, C.; Thoret, S.; Gueritte, F. Tetrahedron Lett. 2000, 41, 5853-5856.
13. For references to cross-coupling reactions with pyrroles, see Refs. 5, 10, 12, 13, 14, 15 and: Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587-3595; Zhou, X.; Tse, M. K.; Wan, T. S. M.; Chan, K. S. J. Org. Chem. 1996, 61, 3590-3593; Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. J. Org. Chem. 1992, 57, 1653-1656; Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497-1499; Dupont, C.; Guenard, D.; Thal, C.; Thoret, S.; Gueritte, F. Tetrahedron Lett. 2000, 41, 5853-5856.
14. For references to cross-coupling reactions with pyrroles, see Refs. 5, 10, 12, 13, 14, 15 and: Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587-3595; Zhou, X.; Tse, M. K.; Wan, T. S. M.; Chan, K. S. J. Org. Chem. 1996, 61, 3590-3593; Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. J. Org. Chem. 1992, 57, 1653-1656; Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497-1499; Dupont, C.; Guenard, D.; Thal, C.; Thoret, S.; Gueritte, F. Tetrahedron Lett. 2000, 41, 5853-5856.
15. For references to cross-coupling reactions with pyrroles, see Refs. 5, 10, 12, 13, 14, 15 and: Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587-3595; Zhou, X.; Tse, M. K.; Wan, T. S. M.; Chan, K. S. J. Org. Chem. 1996, 61, 3590-3593; Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. J. Org. Chem. 1992, 57, 1653-1656; Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497-1499; Dupont, C.; Guenard, D.; Thal, C.; Thoret, S.; Gueritte, F. Tetrahedron Lett. 2000, 41, 5853-5856.
16. For references to cross-coupling reactions with pyrroles, see Refs. 5, 10, 12, 13, 14, 15 and: Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587-3595; Zhou, X.; Tse, M. K.; Wan, T. S. M.; Chan, K. S. J. Org. Chem. 1996, 61, 3590-3593; Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. J. Org. Chem. 1992, 57, 1653-1656; Banwell, M.; Edwards, A.; Smith, J.; Hamel, E.; Verdier-Pinard, P. J. Chem. Soc., Perkin Trans. 1 2000, 1497-1499; Dupont, C.; Guenard, D.; Thal, C.; Thoret, S.; Gueritte, F. Tetrahedron Lett. 2000, 41, 5853-5856.
17. Interestingly, as we were pursuing these investigations, Dr. Cai of Hoffmann-La Roche informed us of a similar observation that they have made in the coupling of 3-bromoindoles in which protection of the indole nitrogen is required to avoid extensive dehalogenation.
18. This deprotection appears to be a thermal reaction. We have noted that simply heating a solution of pyrrole ester 1 in DMF to 120°C for 6 h is sufficient to completely remove the BOC group. Lower temperatures (100°C) do not cleave the BOC group. For similar observations, see: (BOC removal), Fuerstner, A.; Grabowski, J.; Lehmann, C. W. J. Org. Chem. 1999, 64, 8275-8280. (BOC retained), Johnson, C. K.; Stemp, G.; Anand, N.; Stephen, S. C.; Gallagher, T. Synlett 1998, 1025-1027.
19. This deprotection appears to be a thermal reaction. We have noted that simply heating a solution of pyrrole ester 1 in DMF to 120°C for 6 h is sufficient to completely remove the BOC group. Lower temperatures (100°C) do not cleave the BOC group. For similar observations, see: (BOC removal), Fuerstner, A.; Grabowski, J.; Lehmann, C. W. J. Org. Chem. 1999, 64, 8275-8280. (BOC retained), Johnson, C. K.; Stemp, G.; Anand, N.; Stephen, S. C.; Gallagher, T. Synlett 1998, 1025-1027.
20. 3) 161.04, 149.11, 147.72, 127.63, 126.75, 123.54, 118.76, 117.51, 112.15, 111.52, 108.88, 60.43, 55.91, 55.82, 14.41.
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