Synthesis of amino- and hydroxybiphenyls by radical chain reaction of arenediazonium salts

Angewandte Chemie - International Edition

Volumn 47, Issue 47, 2008, Pages 9130-9133

  Wetzel, Alexander ^a   Ehrhardt, Varinia ^a   Heinrich, Markus R ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Aromatic substitution; Biaryls; C C coupling; Radical reactions; Titanium

Indexed keywords

AMINES; REACTION KINETICS; TITANIUM;

ARENEDIAZONIUM IONS; ARENEDIAZONIUM SALTS; AROMATIC SUBSTITUTION; BIARYL PRODUCTS; BIARYLS; C-C COUPLING; CHEMICAL EQUATIONS; PROPAGATION STEPS; RADICAL CHAIN REACTIONS; RADICAL REACTIONS; SYNTHESIS OF;

CHEMICAL REACTIONS;

EID: 56249089672     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803785     Document Type: Article

References (52)

1. M. Beller, C. Bolm, Transition Metals for Organic Synthesis, 2nd ed., Wiley-VCH, Weinheim, 2004.
2. A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004.
3. For recent developments, see: a) T. Dohi, M. Ito, K. Morimoto, M. Iwata, Y. Kita, Angew. Chem. 2008, 120, 1321-1324;
4. Angew. Chem. Int. Ed. 2008, 47, 1301-1304;
5. b) M. Amatore, C. Gosmini, Angew. Chem. 2008, 120, 2119-2122;
6. Angew. Chem. Int. Ed. 2008, 47, 2089-2092;
7. c) L. J. Gooßen, N. Rodríguez, K. Gooßen, Angew. Chem. 2008, 120, 3144-3164;
8. Angew. Chem. Int. Ed. 2008, 47,3100-3120.
9. a) G. Dyker, Handbook of C-H Transformations, Wiley-VCH, Weinheim, 2005;
10. b) L. Ackermann, Top. Organomet. Chem. 2008, 24, 35-60.
11. For recent reports on C-H activation for aryl-aryl coupling, see: a) T. Vogler, A. Studer, Org. Lett. 2008, 10,129-131;
12. b) L. Ackermann, R. Vicente, A. Althammer, Org. Lett. 2008, 10, 2299-2302.
13. st ed., Wiley-VCH, Weinheim, 2001, pp. 62-80;
14. b) W. R. Bowman, J. M. D. Storey, Chem. Soc. Rev. 2007, 36,1803-1822;
15. c) J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, Wiley, Chichester, 1995, pp. 167-180.
16. J. C. Scaiano, L. C. Stewart, J. Am. Chem. Soc. 1983, 105, 3609-3614.
17. For recent examples, see: a) A. Nunez, A. Sanchez, C. Burgos, J. Alvarez-Builla, Tetrahedron 2004, 60, 6217-6224;
18. b) P. T. F. McLoughlin, M. A. Cline, F. Aldabbagh, Tetrahedron 2004, 60, 8065-8071.
19. For a recent example, see: M. L. Bennasar, T. Roca, F. Ferrando, Tetrahedron Lett. 2004, 45, 5605-5609.
20. M. Gomberg, W. E. Bachmann, J. Am. Chem. Soc. 1924, 46, 2339-2343.
21. For the phase-transfer variant of the Gomberg-Bachmann reaction (PTGB), see: J. R. Beadle, S. H. Korzeniowski, D. E. Rosenberg, B. J. Garcia-Slanga, G. W. Gokel, J. Org. Chem. 1984, 49, 1594-1603.
22. R. Pschorr, Ber. Dtsch. Chem. Ges. 1896, 29, 496-501.
23. C. Galli, Chem. Rev. 1988, 88, 765-792.
24. For a recent report on the oxidative rearomatization with dioxygen, see: D. P. Curran, A. I. Keller, J. Am. Chem. Soc. 2006, 128, 13706-13707.
25. For alternative, oxidative rearomatizations, see: a) M. Menes-Arzate, R. Martinez, R. Cruz-Almanza, J. M. Muchowski, Y. M. Osornio, L. D. Miranda, J. Org. Chem. 2004, 69, 4001-4004;
26. b) D. Crich, M. Patel, Org. Lett. 2005, 7, 3625-3628;
27. c) A. L. J. Beckwith, V. W. Bowry, W. R. Bowman, E. Mann, J. Parr, J. M. D. Storey, Angew. Chem. 2004, 116, 97-100;
28. Angew. Chem. Int. Ed. 2004, 43, 95-98;
29. d) M. L. Bennasar, T. Roca, F. Ferrando, J. Org. Chem. 2005, 70, 9077-9080.
30. For earlier work on aryl-aryl coupling by a chain mechanism, see: a) D. Kosynkin, T. M. Bockman, J. K. Kochi, J. Am. Chem. Soc. 1997, 119, 4846-4855;
31. b) R. Bolton, G. H. Williams, Chem. Soc. Rev. 1986, 15, 261-289.
32. S. J. Garden, D. V. Avila, A. L. J. Beckwith, V. W. Bowry, K. U. Ingold, J. Lusztyk, J. Org. Chem. 1996, 61, 805-809.
33. a) M. R. Heinrich, A. Wetzel, M. Kirschstein, Org. Lett. 2007, 9, 3833-3835;
34. b) M. R. Heinrich, O. Blank, S. Wölfel, Org. Lett. 2006, 8, 3323-3325;
35. c) M. R. Heinrich, O. Blank, D. Ullrich, M. Kirschstein, J. Org. Chem. 2007, 72, 9609-9616;
36. d) M. R. Heinrich, O. Blank, A. Wetzel, J. Org. Chem. 2007, 72, 476-484.
37. Dimethoxybenzene is known to reduce pentafluorophenyldiazonium salts to diazenyl radicals. See Ref. [16a].
38. F. Minisci, F. Coppa, F. Fontana, G. Pianese, L. Zhao, J. Org. Chem. 1992, 57, 3929-3933.
39. A. E. Jensen, P. Knochel, J. Organomet. Chem. 2002, 653, 122-128.
40. RN1-type reactions, see: a) R. A. Rossi in Synthetic Organic Photochemistry, Vol. 12 (Eds.: A. Griesbeck, J. Mattay), Marcel Dekker, New York, 2005, pp. 495-527;
41. b) R. A. Rossi, A. B. Pierini, A. B. Peñéñory, Chem. Rev. 2003, 103, 71-167;
42. c) R. A. Rossi, A. B. Pierini, A. N. Santiago in Organic Reactions (Eds.: L. A. Paquette, R. Bittman), Wiley, New York, 1999, pp. 1-272.
43. RN1 conditions, see: P. W. Wojtkowski (E.I. Du Pont de Nemours and Company, Wilmington), US4960957, 1990 [Chem. Abstr. 1990, 114,101343].
44. S. Nerdinger, C. Kendall, R. Marchart, P. Riebel, M. R. Johnson, C.-F. Yin, L. D. Eltis, V. Snieckus, Chem. Commun. 1999, 2259-2260.
45. G. Petrillo, M. Novi, C. Dell'Erba, C. Tavani, Tetrahedron 1991, 47, 9297-9304.
46. a) K. Eicken, M. Rack, F. Wetterich, E. Ammermann, G. Lorenz, S. Strathmann (BASF AG, Ludwigshafen), DE 19735224, 1999 [Chem. Abstr. 1999, 130, 182464];
47. b) K. Eicken, H. Rang, A. Harreus, N. Goetz, E. Ammermann, G. Lorenz, S. Strathmann (BASF AG, Ludwigshafen), DE19531813, 1997 [Chem. Abstr. 1997, 126, 264007].
48. For a recent synthesis of Boscalid, see: A. C. Spivey, C.-C. Tseng, J. P. Hannah, C. J. G. Gripton, P. de Fraine, N. J. Parr, J. J. Scicinski, Chem. Commun. 2007, 2926-2928.
49. P. M. O'Neill, D. J. Willock, S. R. Hawley, P. G. Bray, R. C. Storr, S. A. Ward, B. K. Park, J. Med. Chem. 1997, 40, 437-448.
50. a) G. A. Biagini, P. M. O'Neill, A. Nzila, S. A. Ward, P. G. Bray, Trends Parasitol. 2003, 19, 479-487;
51. b) O. V. Miroshnikova, T. H. Hudson, L. Gerena, D. E. Kyle, A. J. Lin, J. Med. Chem. 2007, 50, 889-896.
52. The clinical use of tebuquine is hindered by side effects.