Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process

Angewandte Chemie - International Edition

Volumn 54, Issue 36, 2015, Pages 10587-10591

  Pichette Drapeau, Martin ^a,b   Fabre, Indira ^c,d   Grimaud, Laurence ^c   Ciofini, Ilaria ^d   Ollevier, Thierry ^b   Taillefer, Marc ^a  

^a INSTITUT CHARLES GERHARDT   (France)

^b UNIVERSITÉ LAVAL   (Canada)

^c ECOLE NORMALE SUPÉRIEURE   (France)

^d PSL RESEARCH UNIVERSITY   (France)

Author keywords

arylation; C C coupling; ketones; reaction mechanisms

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; KETONES; MECHANICS; METAL HALIDES;

ARYL KETONES; ARYLATIONS; C-C COUPLING; COST ECONOMICS; MECHANISTIC STUDIES; METAL-FREE CONDITIONS; RADICAL PROCESS; REACTION MECHANISM;

TRANSITION METALS;

EID: 84940446640     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201502332     Document Type: Article

References (60)

1. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082
2. C. C. C. Johansson, T. J. Colacot, Angew. Chem. Int. Ed. 2010, 49, 676
3. Angew. Chem. 2010, 122, 686.
4. M. F. Semmelhack, R. D. Stauffer, T. D. Rogerson, Tetrahedron Lett. 1973, 14, 4519.
5. M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108
6. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 12382
7. T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. Int. Ed. Engl. 1997, 36, 1740
8. Angew. Chem. 1997, 109, 1820.
9. G. A. Grasa, T. J. Colacot, Org. Lett. 2007, 9, 5489
10. K. D. Hesp, R. J. Lundgren, M. Stradiotto, J. Am. Chem. Soc. 2011, 133, 5194
11. M. Henrion, M. J. Chetcuti, V. Ritleng, Chem. Commun. 2014, 50, 4624.
12. A. Tlili, G. Danoun, F. Monnier, M. Taillefer, FR, 2012 -055275, PCT/EP 2013 -061697
13. G. Danoun, A. Tlili, F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2012, 51, 12815
14. Angew. Chem. 2012, 124, 12987.
15. J. F. Bunnett, Acc. Chem. Res. 1978, 11, 413
16. R. A. Rossi, A. B. Pierini, A. B. Peñéñory, Chem. Rev. 2003, 103, 71.
17. C. Galli, J. F. Bunnett, J. Org. Chem. 1984, 49, 3041
18. C. Galli, P. Gentili, J. Chem. Soc. Perkin Trans. 2 1993, 1135
19. M. A. Nazareno, R. A. Rossi, Tetrahedron Lett. 1994, 35, 5185.
20. J. F. Bunnett, J. E. Sundberg, J. Org. Chem. 1976, 41, 1702
21. R. A. Rossi, R. H. de Rossi, A. F. Lopez, J. Am. Chem. Soc. 1976, 98, 1252
22. J. F. Bunnett, R. G. Scamehorn, R. P. Traber, J. Org. Chem. 1976, 41, 3677
23. M. P. Moon, J. F. Wolfe, J. Org. Chem. 1979, 44, 4081
24. M. F. Semmelhack, T. Bargar, J. Am. Chem. Soc. 1980, 102, 7765
25. G. L. Borosky, A. B. Pierini, R. A. Rossi, J. Org. Chem. 1992, 57, 247
26. M. T. Baumgartner, L. B. Jiménez, A. B. Pierini, R. A. Rossi, J. Chem. Soc. Perkin Trans. 2 2002, 1092.
27. R. G. Scamehorn, J. F. Bunnett, J. Org. Chem. 1977, 42, 1449
28. D. R. Carver, A. P. Komin, J. S. Hubbard, J. F. Wolfe, J. Org. Chem. 1981, 46, 294
29. R. G. Scamehorn, J. M. Hardacre, J. M. Lukanich, L. R. Sharpe, J. Org. Chem. 1984, 49, 4881
30. E. Austin, C. G. Ferrayoli, R. A. Alonso, R. A. Rossi, Tetrahedron 1993, 49, 4495.
31. The first α-arylation of aromatic ketones induced by microwave irradiation has recently been described. Owing to competing reduction, low to fair yields were obtained except for the formation of 1-methyl-3-phenylindolin-2-one (100% yield); see:, S. M. Soria-Castro, D. A. Caminos, A. B. Peñéñory, RSC Adv. 2014, 4, 17490.
32. C. Dell'Erba, M. Novi, G. Petrillo, C. Tavani, Tetrahedron 1993, 49, 235
33. T. Miyoshi, S. Sato, H. Tanaka, C. Hasegawa, M. Ueda, O. Miyata, Tetrahedron Lett. 2012, 53, 4188.
34. E. Shirakawa, X. Zhang, T. Hayashi, Angew. Chem. Int. Ed. 2011, 50, 4671
35. Angew. Chem. 2011, 123, 4767
36. A. Beyer, J. Buendia, C. Bolm, Org. Lett. 2012, 14, 3948.
37. I. Thomé, A. Nijs, C. Bolm, Chem. Soc. Rev. 2012, 41, 979.
38. To determine whether palladium impurities (in resublimed KOtBu, distilled solvents, or purified reagents) might catalyze the transformation, the reaction of PhI with propiophenone was performed in the presence of palladium (under the conditions of Table 1, entry 3 at 23°C). Whereas the blank experiment without Pd gave the expected phenylated propiophenone 1 in 65% yield after 13 hours, only 1% of 1 was obtained under the same conditions in the presence of [Pd(dba)2] (10 mol%, dba=dibenzylideneacetone). Therefore, the palladium complex dramatically slowed down the reaction. This result is a significant indication that the reaction is metal-free.
39. Starting from PhI, the expected product was obtained in very low yield under our standard conditions when dialkyl ketones were employed, whereas with α-tetralone, no reaction was observed.
40. M. C. Willis, D. Taylor, A. T. Gillmore, Org. Lett. 2004, 6, 4755
41. C. Eidamshaus, J. D. Burch, Org. Lett. 2008, 10, 4211.
42. For the synthesis of an isoquinoline, see the Supporting Information.
43. For a synthetic review, see:, K. M. Kasiotis, S. A. Haroutounian, Curr. Org. Chem. 2012, 16, 335.
44. M. Baum, Lancet 1985, 1, 836.
45. G. D. Bedford, D. N. Richardson, Nature 1966, 212, 733.
46. Catalytic and stoichiometric amounts of diamine and phenanthroline-type ligands were added to reactions under the optimized conditions. However, no increases in yield or reaction rate were observed.
47. C.-L. Sun, Z.-J. Shi, Chem. Rev. 2014, 114, 9219; for critical comments, see
48. A. Studer, D. P. Curran, Nat. Chem. 2014, 6, 765
49. A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2011, 50, 5018
50. Angew. Chem. 2011, 123, 5122; for a mechanistic study, see
51. H. Yi, A. Jutand, A. Lei, Chem. Commun. 2015, 51, 545.
52. J. Cuthbertson, V. J. Gray, J. D. Wilden, Chem. Commun. 2014, 50, 2575.
53. S. Zhou, G. M. Anderson, B. Mondal, E. Doni, V. Ironmonger, M. Kranz, T. Tuttle, J. A. Murphy, Chem. Sci. 2014, 5, 476.
54. W.-t. Wei, X.-j. Dong, S.-z. Chen, Y.-y. Chen, X.-j. Zhang, M. Yan, Org. Lett. 2013, 15, 6018.
55. J. T. Reeves, Z. Tan, M. A. Herbage, Z. S. Han, M. A. Marsini, Z. Li, G. Li, Y. Xu, K. R. Fandrick, N. C. Gonnella, S. Campbell, S. Ma, N. Grinberg, H. Lee, B. Z. Lu, C. H. Senanayake, J. Am. Chem. Soc. 2014, 135, 5565.
56. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999.
57. G. Silvestri, S. Gambino, G. Filardo, A. Gulotta, Angew. Chem. Int. Ed. Engl. 1984, 23, 979
58. Angew. Chem. 1984, 96, 978
59. O. Sock, M. Troupel, J. Périchon, Tetrahedron Lett. 1985, 26, 1509.
60. The results presented in this Communication are protected as a patent: "Transition-metal-free α-arylation of enolisable ketones", M. Pichette Drapeau, T. Ollevier, M. Taillefer, FR 1457458 CNRS/ENSCM/Univ. Laval, 2014.