Combined Directed ortho Metalation/Suzuki-Miyaura cross-coupling strategies. Regiospecific synthesis of chlorodihydroxybiphenyls and polychlorinated biphenyls

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 5960-5967

  Nerdinger, S ^a   Kendall, C ^h   Cai, X ^b   Marchart, R ^d   Riebel, P ^e   Johnson, M R ^f   Yin, C F ^g   Henaff N ^b   Eltis, L D ^c   Snieckus, V ^b  

^a NOVARTIS PHARMA AG   (Switzerland)

^b QUEEN S UNIVERSITY   (Canada)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^d VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^e DSM RESOLVE   (Netherlands)

^f ALBANY MOLECULAR RESEARCH INC   (United States)

^g PFIZER INC   (United States)

^h Wyeth Research Canada   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATION; CHLORODIHYDROXYBIPHENYLS; CROSS-COUPLING STRATEGIES; ISOMERIC MONOCHLORO;

ISOMERIZATION; ISOMERS; ITERATIVE METHODS; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

POLYCHLORINATED BIPHENYLS;

BIPHENYL DERIVATIVE; CHLORODIHYDROXYBIPHENYL DERIVATIVE; POLYCHLORINATED BIPHENYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ISOMER; REACTION ANALYSIS; SUZUKI REACTION; SYNTHESIS;

BIPHENYL COMPOUNDS; CATECHOLS; CHEMISTRY, ORGANIC; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; OXIDATION-REDUCTION; POLYCHLORINATED BIPHENYLS; STEREOISOMERISM;

EID: 34547626461     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062543i     Document Type: Article

References (47)

1. (a) Dagley, S. In The Bacteria; Sokatch, J. R., Ornston, L. N., Eds.; Academic Press: New York, 1986; pp 527-555.
2. (b) Timmis, K. N. Steffan, R. J.; Unterman, R. Annu. Rev. Microbiol. 1994, 48, 525.
3. (a) Ayres, D.; Hellier, D. Dictionary of Environmentally Important Chemicals; Blackie: New York, 1998; p 245.
4. (b) Tiedje, J. M.; Quensen, J. F., III Chee-Sanford, J.; Schimel, J. P.; Boyd, S. A. Biodegradation 1993, 4, 231-240.
5. (c) Erickson, M. D. Analytical Chemistry of PCBs; Lewis: Boca Raton, FL, 1992.
6. (d) Abramowicz, D. A. Crit. Rev. Biotechnol. 1990, 10, 241.
7. McFarland, V. A.; Clarke, J. U. Environ. Health Perspect. 1989, 81, 225.
8. Que, L.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607.
9. Bugg T. D. H.; Winfield, C. J. Nat. Prod. Rep. 1998, 513.
10. Timmis, K. N.; Steffan, R. J.; Unterman, R. Annu. Rev. Microbiol. 1994, 48, 525.
11. Focht, D. D. Curr. Opin. Biotechnol. 1995, 6, 341.
12. For recent mechanistic work, see: Li, J.-J.; Bugg, T. D. H. J. Chem. Soc., Chem. Commun. 2005, 130.
13. Furukawa, K. Curr. Opin. Biotechnol. 2000, 11, 244.
14. Furukawa, K. Trends Biotechnol. 2003, 21, 187-190.
15. Furukawa, K. J. Gen. Appl. Microbiol. 2000, 46, 283-296.
16. Fortin, P. D.; Lo, A. T. F.; Haro, M. A.; Kaschabek, S. R.; Reineke, W.; Eltis, L. D. J. Bacteriol. 2005, 187, 415-421.
17. Vaillancourt, F. H.; Haro, M.-A.; Drouin, N. M.; Karim, Z.; Maaroufi, H.; Eltis, L. D. J. Bacteriol. 2003, 185, 1253-1260.
18. Seah, S. Y. K.; Labbé, G.; Kaschabek, S. R.; Reifenrath, F.; Reineke, W.; Eltis, L. D. J. Bacteriol. 2001, 183, 1511-1516.
19. (a) Dai, S.; Vaillancourt, F. H.; Maaroufi, H.; Drouin, N. M.; Neau, D. B.; Snieckus, V.; Bolin, J. T.; Eltis, L. D. Nature Struct. Biol. 2002, 9, 934.
20. (b) Seah, S. Y. K.; Labbé, G.; Nerdinger, S.; Johnson, M. R.; Snieckus, V.; Eltis, L. D. J. Biol. Chem. 2000, 275, 15701.
21. (c) Vaillancourt, F. H.; Han, S.; Fortin, P. D.; Bolin, J. T.; Eltis, L. D. J. Biol. Chem. 1998, 273, 34887.
22. (d) Seah, S. Y. K.; Terracina, G.; Bolin, J. T.; Riebel, P.; Snieckus, V.; Eltis, L. D. J. Biol. Chem. 1998, 273, 22943.
23. For a review that encompasses other named cross-coupling reactions initiated by DoM, see: (a) Anctil, E.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150-160.
24. (b) Anctil, E. J.-G.; Snieckus, V. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Diederich, F.,de Meijere, A., Eds.; Wiley-VC: New York, 2004; pp 761-814.
25. For a specialized treatise, see: Cepanec, I. Synthesis of Biaryls: Elevier: Amsterdam, The Netherlands, 2004.
26. (a) For a preliminary communication, see: Nerdinger, S.; Kendall, C.; Marchhart, R.; Riebel, P.; Johnson, M. R.; Yin, C.-F.; Eltis, L. D.; Snieckus, V. J. Chem. Soc., Chem. Commun. 1999, 2259.
27. More recently, Robertson has reported on the preparation of mono- and dihydroxylated PCB metabolites by a Suzuki-Miyaura cross-coupling protocol, see: (b) Lehmler, H.-J.; Robertson, L. W. Chemosphere 2001, 45, 137
28. 3-isotopomer chloro-DHBs, see: (c) Lin, P.-H.; Sangaiah, R.; Ranasinghe, A.; Ball, L. M.; Swenberg, J. A.; Gold, A. Org. Biomol. Chem. 2004, 2, 2624.
29. Bauer, U.; Amaro, A. R.; Robertson, L. W. Chem. Res. Toxicol. 1995, 8, 92.
30. Lehmler, H.-J.; Robertson, L. W. Chemosphere 2001, 45, 137.
31. For a qualitative ranking of DMG hierarchy, see: Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206.
32. Alo, B. I.; Kandil, A.; Patil, P. A.; Sharp, M. J.; Siddiqui, M. A.; Josephy, P. D.; Snieckus, V. J. Org. Chem. 1991, 56, 3763.
33. For comparable cases, see: (a) Harvey, R. G.; Cortez, C.; Ananthanarayan, T. P.; Schmolka, S. J. Org. Chem. 1988, 53, 3936.
34. (b) Weeratunga, G.; Jaworska-Sobiesiak, A.; Horne, S; Rodrigo, R. Can. J. Chem. 1987, 65, 2019.
35. Fitt, J. J.; Gschwend, H. W.; Hamdan, A.; Boyer, S. K.; Haider, H. M. J. Org. Chem. 1982, 47, 3658.
36. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
37. (a) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
38. (b) Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
39. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.
40. Prevot-Halter, I.; Smith, T. J.; Weiss, J. J. Org. Chem. 1997, 62, 2186.
41. Allen, G.; Bruce, J. M. J. Chem. Soc. 1963, 1757.
42. Bruce, J. M.; Sutcliffe, F. K. J. Chem. Soc. 1955, 4435.
43. Labidalle, S.; Zhang, Y.-M.; Reynet, A.; Moskowitz, H.; Vierfond, J.-M.; Miocque, M. Tetrahedron 1988, 44, 1159.
44. Plaumann, H. P.; Rodrigo, R. Pol. J. Chem. 1979, 53, 201.
45. Yanagisawa, M.; Hayamizu, K.; Yamamoto, O. Magn. Reson. Chem. 1987, 25, 184.
46. Bolgar, M.; Cunningham, J.; Cooper, R.; Kozloski, R.; Hubball, J.; Miller, D. P.; Crone, T.; Kimball, H.; Janooby, A.; Miller, B.; Fairless, B. Chemosphere 1995, 31, 2687.
47. See: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.