Formation of four different aromatic scaffolds from nitriles through tandem divergent catalysis

Angewandte Chemie - International Edition

Volumn 53, Issue 25, 2014, Pages 6435-6438

  Kim, Ju Hyun ^a   Bouffard, Jean ^a   Lee, Sang Gi ^a  

^a Ewha Womans University   (South Korea)

Author keywords

aromatics; divergency; nitriles; palladium; tandem reactions

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; CYANIDES; PALLADIUM; PALLADIUM COMPOUNDS; SCAFFOLDS;

AROMATICS; DIVERGENCY; NITRILES; PALLADIUM CATALYST; PALLADIUM-CATALYZED REACTIONS; REFORMATSKY REAGENTS; SEQUENTIAL REACTION; TANDEM REACTION;

REACTION INTERMEDIATES;

BROMIDE; NITRILE; PALLADIUM; ZINC BROMIDE; ZINC DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

BROMIDES; CATALYSIS; MOLECULAR STRUCTURE; NITRILES; PALLADIUM; ZINC COMPOUNDS;

EID: 84902345562     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201403698     Document Type: Article

References (57)

1. For a review on catalyst-controlled reactions, see:, J. Mahatthananchai, A. M. Dumas, J. W. Bode, Angew. Chem. 2012, 124, 11114
2. Angew. Chem. Int. Ed. 2012, 51, 10954.
3. For selected recent examples of catalyst-controlled reactions, see:a) J.-F. Brazeau, S. Zhang, I. Colomer, B. K. Corkey, F. D. Toste, J. Am. Chem. Soc. 2012, 134, 2742
4. C. Zheng, D. Wang, S. S. Stahl, J. Am. Chem. Soc. 2012, 134, 16496
5. A. Di Giuseppe, R. Castarlenas, J. J. Pérez-Torrente, M. Crucianelli, V. Polo, R. Sancho, F. J. Lahoz, L. A. Oro, J. Am. Chem. Soc. 2012, 134, 8171
6. Y. Yang, S. L. Buchwald, J. Am. Chem. Soc. 2013, 135, 10642
7. B. Li, Y. Park, S. Chang, J. Am. Chem. Soc. 2014, 136, 1125
8. P.-h. Chen, T. Xu, G. Dong, Angew. Chem. 2014, 126, 1700
9. Angew. Chem. Int. Ed. 2014, 53, 1674.
10. For recent leading reviews, see:a) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
11. Angew. Chem. Int. Ed. 2006, 45, 7134
12. B. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439
13. J. Zhou, Chem. Asian J. 2010, 5, 422
14. L.-Q. Lu, J. R-R. Chen, W.-J. Xiao, Acc. Chem. Res. 2012, 45, 1278.
15. J. H. Kim, S.-g. Lee, Org. Lett. 2011, 13, 1350
16. J. H. Kim, S.-g. Lee, Synthesis 2012, 1464
17. Y. S. Chun, J. H. Kim, S. Y. Choi, Y. O. Ko, S.-g. Lee, Org. Lett. 2012, 14, 6358
18. Y. S. Chun, Z. Xuan, J. H. Kim, S.-g. Lee, Org. Lett. 2013, 15, 3162.
19. Y. S. Chun, Y. O. Ko, H. Shin, S.-g. Lee, Org. Lett. 2009, 11, 3414
20. J. H. Kim, Y. S. Chun, S.-g. Lee, J. Org. Chem. 2013, 78, 11483.
21. The Chemistry of Anilines, Parts 1 and 2, (Ed.:, Z. Rappoport,), Wiley, New York, 2007
22. M. Enders, R. W. Baker, Curr. Org. Chem. 2006, 10, 937
23. R. A. Jones, Pyrroles, Part II, Wiley, New York, 1992
24. T. Eicher, S. Hauptmann, A. Speicher, The Chemistry of Heterocycles, 2 nd ed., Wiley-VCH, Weinheim, 2003.
25. CCDC 975343 (3a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. See also the Supporting Information.
26. For recent examples of the synthesis of 1-aminonaphthalenes by Pd-catalyzed aerobic dehydrogenation of tetralone pyvaloyl oximes, see:, W. P. Hong, A. V. Isoub, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 13664.
27. F. Ozawa, A. Kubo, T. Hayashi, Chem. Lett. 1992, 2177
28. C. Amatore, E. Carre, A. Jutand, M. A. M'Barki, Organometallics 1995, 14, 1818
29. C. Amatore, A. Jutand, M. J. Medeiros, New J. Chem. 1996, 20, 1143
30. B. Fors, P. Krattiger, E. Strieter, S. L. Buchwald, Org. Lett. 2008, 10, 3505.
31. For solvent-controlled divergent catalytic reactions, see: a) N. P. Grimster, C. Gauntlett, C. R. A. Godfrey, M. J. Gaunt, Angew. Chem. 2005, 117, 3185
32. Angew. Chem. Int. Ed. 2005, 44, 3125
33. M. E. Krafft, D. V. Vidhani, J. W. Cran, M. Manoharan, Chem. Commun. 2011, 47, 6707
34. Y. Zhu, Y. Wei, Eur. J. Org. Chem. 2013, 4503.
35. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009
36. J. T. Link, L. Overman, in Metal-Catalyzed Cross-Coupling Reactions (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, New York, 1998.
37. Z. Owczarczyk, F. Lamaty, E. J. Vawterr, E. Negishi, J. Am. Chem. Soc. 1992, 114, 10091.
38. For an intramolecular Heck reaction involving β-carbon cleavage of a σ-carbopalladate, see:, S. W. Youn, B. S. Kim, A. R. Jagdale, J. Am. Chem. Soc. 2012, 134, 11308.
39. B. Burns, R. Grigg, P. Ratananukul, V. Sridhran, P. Stevenson, T. Worakun, Tetrahedron Lett. 1988, 29, 4329
40. L. F. Tietze, L. R. Schimpf, Chem. Ber. 1994, 127, 2325
41. H. Finch, N. A. Pegg, B. Evans, Tetrahedron Lett. 1993, 34, 8352.
42. For selected reviews, see:a) A. Minatti, K. Muñiz, Chem. Soc. Rev. 2007, 36, 1142
43. V. Kotov, C. C. Scarborough, S. S. Stahl, Inorg. Chem. 2007, 46, 1910
44. R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981.
45. For selected reviews, see:a) L. Jiang, S. L. Buchwald, Metal-Catalyzed Cross Coupling Reactions, Vol. 2, 2 nd ed., Wiley-VCH, Weinheim, 2004, pp. 699-760
46. J. F. Hartwig, Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, Wiley-Interscience, New York, 2002, pp. 1051-1069.
47. This type of conditions has been used for the aza-Wacker-type intramolecular cyclization of N-arylated 2-vinylated anilines resulting in indole derivatives. See:, D. Tsvelikhovsky, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 14048; addition/correction
48. J. Am. Chem. Soc. 2012, 134, 16917; for the pioneering work of Hegedus, see
49. L. S. Hegedus, Tetrahedron 1984, 40, 2415.
50. V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047
51. D. W. Old, J. P. Wolf, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722
52. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369.
53. II-catalyzed 5-endo-trig cyclization, see:, S. R. Kandukuri, J. A. Schiffner, M. Oestreich, Angew. Chem. 2012, 124, 1291
54. Angew. Chem. Int. Ed. 2012, 51, 1265.
55. II-catalyzed reactions using molecular oxygen as the sole oxidant, see:a) A. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851
56. Z. Shi, C. Zhang, Y. Cui, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381
57. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780.