Palladium/norbornene-catalyzed synthesis of heteroatom-containing o-teraryls from aryl iodides and heteroarenes through double C-H activation in sequence

Chemistry - A European Journal

Volumn 15, Issue 32, 2009, Pages 7850-7853

  Della Ca, Nicola ^a   Maestri, Giovanni ^a   Catellani, Marta ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

C C coupling reaction; C H activation; Catalysis; Heterocyclic compounds; Palladium

Indexed keywords

ALKYL GROUPS; ARYL IODIDES; BOND FORMATION; C-C COUPLING REACTION; C-H ACTIVATION; C-H FUNCTIONALIZATION; CATALYZED SYNTHESIS; DIFFERENT DISTRIBUTIONS; HETEROARENES; HETEROATOMS; HETEROCYCLIC COMPOUNDS; IODOBENZENE; NORBORNENES; OXIDATIVE ADDITION PRODUCTS; PALLADIUM ACETATE; SECONDARY PRODUCT; STERIC HINDRANCES;

ACTIVATION ANALYSIS; CATALYSIS; CATALYSTS; COMPLEXATION; PALLADIUM;

ORGANOMETALLICS;

HETEROCYCLIC COMPOUND; IODINATED HYDROCARBON; NORBORNANE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; NORBORNANES; PALLADIUM;

EID: 68349104058     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900843     Document Type: Article

References (40)

1. L. Ackerman, Modern Arylation Methods, Wiley-VCH, Weinheim, 2009.
2. a) B. Liégault, D. Lapointe, L. Caron, A. Vlassova, K. Fagnou, J. Org. Chem. 2009, 74, 1826-1834;
3. b) M. Lafrance, D. Lapointe, K. Fagnou, Tetrahedron 2008, 64, 6015-6020;
4. c) J. C Lewis, R. G. Bergman, J A. Ellman, Acc. Chem. Res. 2008, 41, 1013-1025;
5. d) G. B. Bajracharya, O. Daugulis, Org. Lett. 2008, 10, 4625-4628;
6. e) K. Kakiuchi, T. Kochi, Synthesis 2008, 3013-3039;
7. f) R. B. Bedford, M. Betham, J. P. H. Charmant, A. L. Weeks, Tetrahedron 2008, 64, 6038-6050;
8. g)F. Bellina, S. Cauteruccio, R. Rossi, Curr. Org. Chem. 2008, 12, 774-790;
9. h) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238;
10. i) I. V. Seregin, V. Gevorgian, Chem. Soc. Rev. 2007, 36, 1173-1193;
11. j) I. J. Fairlamb, Chem. Soc. Rev. 2007, 36, 10361045;
12. k) K. Godula, D. Sames, Science 2006, 312, 67-72;
13. M. Miura, T. Satoh, Top. Organomet. Chem. 2005, 14, 55-83;
14. m) G. Dyker, Handbook of C-H Transformations, Wiley, Weinheim, 2005;
15. n) J. Tsuji, Palladium Reagents and Catalysts, Wiley, New York, 2004;
16. o) M. Beller, C. Bolm, Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, 2nd ed., Wiley-VCH, Weinheim, 2004;
17. p) J. Hassan, M. Sevignon, C. Gozzi, E. Schultz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469.
18. a) M. Catellani, E. Motti, N. Della Ca', Acc. Chem. Res. 2008, 41, 1512-1522;
19. b) M. Catellani, Top. Organomet. Chem. 2005, 14, 21-53;
20. c) F. Faccini, E. Motti, M. Catellani, J. Am. Chem. Soc. 2004, 226, 7879;
21. d) E. Motti, G. Ippomei, S. Deledda, M. Catellani, Synthesis 2003, 2671-2678;
22. e) E. Motti, F. Faccini, I. Ferrari, M. Catellani, R. Ferraccioli, Org. Lett. 2006, 8, 3967-3970.
23. a) P. Fitton, E. A. Rick, J. Organomet. Chem. 1971, 28, 287-291;
24. b) A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 1394413945;
25. c) C Amatore, A. Jutand, Ace. Chem. Res. 2000, 33, 314-321.
26. a) H. Horino, M. Arai, N. Inoue, Tetrahedron Lett. 1974, 15, 647650;
27. b) C-S. Li, C-H. Cheng, F.-L. Liao, S.-L. Wang, Chem. Commun. 1991, 710-712;
28. c) M. Portnoy, Y. Ben-David, I. Rousso, D. Milstein, Organometallics 1994, 13, 3465-3479;
29. d) M. Catellani, C. Mealli, E. Motti, P. Paoli, E. Perez-Carreno, P. S. Pregosin, J. Am. Chem. Soc. 2002, 124, 4336-4346.
30. a) I. P. Beletskaya, A. V. Cheprakov, /. Organomet. Chem. 2004, 689, 4055-4082;
31. b) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1992, 425, 151-154;
32. c) M. Catellani, G.P. Chiusoli, J. Organomet. Chem. 1988, 346, C27-C30;
33. d) C.-H. Liu, C.-S. Li, C-H. Cheng, Organometallics 1994, 13, 18-20.
34. a) G. Dyker, Angew. Chem. 1999, 111, 1808-1822;
35. Angew. Chem. Int. Ed. 1999, 38, 1699-1712;
36. b) F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077-1101;
37. c) A. R. Dick, M.S. Sanford, Tetrahedron 2006, 62, 2439-2463.
38. a) M. Catellani, L. Ferioli, Synthesis 1996, 769-772;
39. b) S. Deledda, E. Motti, M. Catellani, Can. J. Chem. 2005, 83, 741-747.
40. M. Catellani, E. Motti, S. Ghelli, Chem. Commun. 2000, 2001-2002.