A general palladium-catalyzed method for alkylation of heteroarenes using secondary and tertiary alkyl halides

Angewandte Chemie - International Edition

Volumn 53, Issue 49, 2014, Pages 13573-13577

  Wu, Xiaojin ^a   See, Jessica Wei Ting ^a   Xu, Kai ^a   Hirao, Hajime ^a   Roger, Julien ^b   Hierso, Jean Cyrille ^b   Zhou, Jianrong ^a  

^a Nanyang Technological University   (Singapore)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Alkyl radicals; C H activation; Heterocycles; Palladium; Single electron transfer

Indexed keywords

ACTIVATION ANALYSIS; ALKYLATION; CATALYSTS; PALLADIUM;

ALKYL HALIDES; ALKYL RADICAL ADDITION; ALKYL RADICALS; C-H ACTIVATION; HETEROCYCLES; PALLADIUM CATALYST; PALLADIUM-CATALYZED; SINGLE ELECTRON TRANSFER;

FREE RADICAL REACTIONS;

HALOGEN; HETEROCYCLIC COMPOUND; PALLADIUM;

ALKYLATION; CHEMISTRY;

ALKYLATION; HALOGENS; HETEROCYCLIC COMPOUNDS; PALLADIUM;

EID: 84915750313     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201408355     Document Type: Article

References (76)

1. Recent reviews: a) L. Ackermann, Chem. Commun. 2010, 46, 4866;
2. b) X. L. Hu, Chem. Sci. 2011, 2, 1867;
3. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879.
4. a) M. Rueping, B. J. Nachtsheim, Beilstein J. Org. Chem. 2010, 6, 6;
5. b) R. Taylor, Electrophilic Aromatic Substitution, Wiley, Chichester, 1990;
6. c) G. A. Olah, Fridel-Crafts Chemistry, Wiley, New York, 1973;
7. d) recent use of metal halides or triflate precatalysts:M. Rueping, B. J. Nachtsheim, T. Scheidt, Org. Lett. 2006, 8, 3717;
8. e) I. Iovel, K. Mertins, J. Kischel, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2005, 44, 3913;
9. Angew. Chem. 2005, 117, 3981;
10. f) K. Mertins, I. Iovel, J. Kischel, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2005, 44, 238;
11. Angew. Chem. 2005, 117, 242;
12. g) Y.-P. Xiao, X.-Y. Liu, C.-M. Che, J. Organomet. Chem. 2009, 694, 494.
13. a)W. R. Bowman, J. M. D. Storey, Chem. Soc. Rev. 2007, 36, 1803;
14. b) K. S. K. Murthy, E. E. Knaus, Drug Dev. Res. 1999, 46, 155;
15. c) F. Minisci, E. Vismara, F. Fontana, Heterocycles 1989, 28, 489;
16. d) M. A. J. Duncton, MedChemComm 2011, 2, 1135;
17. recent examples: e) F. O'Hara, D. G. Blackmond, P. S. Baran, J. Am. Chem. Soc. 2013, 135, 12122;
18. f) Y. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herle, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95;
19. g) G. A. Molander, V. Colombel, V. A. Braz, Org. Lett. 2011, 13, 1852.
20. Examples: a) T. Andou, Y. Saga, H. Komai, S. Matsunaga, M. Kanai, Angew. Chem. Int. Ed. 2013, 52, 3213;
21. Angew. Chem. 2013, 125, 3295;
22. b) Y. Nakao, N. Kashihara, K. S. Kanyiva, T. Hiyama, Angew. Chem. Int. Ed. 2010, 49, 4451;
23. Angew. Chem. 2010, 122, 4553;
24. c) J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013;
25. d) D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624;
26. e) Z. Ding, N. Yoshikai, Angew. Chem. Int. Ed. 2013, 52, 8574;
27. Angew. Chem. 2013, 125, 8736;
28. f) Y. Nakao, H. Idei, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 15996;
29. g) N. A. Foley, J. P. Lee, Z. Ke, T. B. Gunnoe, T. R. Cundari, Acc. Chem. Res. 2009, 42, 585;
30. h) C. S. Sevov, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 2116;
31. i) C. Liu, C. F. Bender, X. Han, R. A. Widenhoefer, Chem. Commun.
32. Alkylation using alkyl halides: a) P. Ren, I. Salihu, R. Scopelliti, X. Hu, Org. Lett. 2012, 14, 1748;
33. b) T. Yao, K. Hirano, T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 12307;
34. c) L. Ackermann, B. Punji,W. Song, Adv. Synth. Catal. 2011, 353, 3325;
35. d) C. Verrier, C. Hoarau, F. Marsais, Org. Biomol. Chem. 2009, 7, 647;
36. e) O. Vechorkin, V. Proust, X. Hu, Angew. Chem. Int. Ed. 2010, 49, 3061;
37. Angew. Chem. 2010, 122, 3125. Alkylation using Ntosylhydrozones
38. f) X. Zhao, G. Wu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 3296;
39. g) T. Yao, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 775;
40. Angew. Chem. 2012, 124, 799;
41. h)W.-C. Lee, C.-H. Wang, Y.-H. Lin, W.-C. Shih, T.-G. Ong, Org. Lett. 2013, 15, 5358.
42. Examples: a) Y. Aihara, N. Chatani, J. Am. Chem. Soc. 2013, 135, 5308;
43. b) K. Gao, N. Yoshikai, J. Am. Chem. Soc. 2013, 135, 9279;
44. c) L. Ilies, T. Matsubara, S. Ichikawa, S. Asako, E. Nakamura, J. Am. Chem. Soc. 2014, 136, 13126.
45. P. M. Perez Garcia, T. Di Franco, A. Orsino, P. Ren, X. Hu, Org. Lett. 2012, 14, 4286.
46. B. Xiao, Z.-J. Liu, L. Liu, Y. Fu, J. Am. Chem. Soc. 2013, 135, 616.
47. a) D. Roy, S. Mom, M. Beaupérin, H. Doucet, J.-C. Hierso, Angew. Chem. Int. Ed. 2010, 49, 6650;
48. Angew. Chem. 2010, 122, 6800;
49. b) V. A. Zinovyeva, S. Mom, S. Fournier, C. H. Devillers, H. Cattey, H. Doucet, J.-C. Hierso, D. Lucas, Inorg. Chem. 2013, 52, 11923;
50. c) J.-C. Hierso, M. Beaupérin, P. Meunier, Eur. J. Inorg. Chem. 2007, 3767.
51. Examples: a) J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 5332;
52. b) B.-T. Guan, Z. Hou, J. Am. Chem. Soc. 2011, 133, 18086;
53. c) L. D. Tran, O. Daugulis, Org. Lett. 2010, 12, 4277;
54. d) Y. Nakao, Y. Yamada, N. Kashihara, T. Hiyama, J. Am. Chem. Soc. 2010, 132, 13666.
55. Nickel-catalyzed coupling of indoles and a-bromoesters: A. Nakatani, K. Hirano, T. Satoh, M. Miura, Chem. Eur. J. 2013, 19, 7691.
56. a)W. Song, S. Lackner, L. Ackermann, Angew. Chem. Int. Ed. 2014, 53, 2477;
57. Angew. Chem. 2014, 126, 2510;
58. b) B. Punji, W. Song, G. A. Shevchenko, L. Ackermann, Chem. Eur. J. 2013, 19, 10605.
59. a) L. Jiao, E. Herdtweck, T. Bach, J. Am. Chem. Soc. 2012, 134, 14563;
60. b) L. Jiao, T. Bach, Angew. Chem. Int. Ed. 2013, 52, 6080;
61. Angew. Chem. 2013, 125, 6196.
62. A. C. Bissember, A. Levina, G. C. Fu, J. Am. Chem. Soc. 2012, 134, 14232.
63. Examples: a) Y. Zou, J. Zhou, Chem. Commun. 2014, 50, 3725;
64. b) C. M. McMahon, E. J. Alexanian, Angew. Chem. Int. Ed. 2014, 53, 5974;
65. Angew. Chem. 2014, 126, 6084;
66. c) K. S. Bloome, R. L. McMahen, E. J. Alexanian, J. Am. Chem. Soc. 2011, 133, 20146;
67. d) I. Ryu, S. Kreimerman, F. Araki, S. Nishitani, Y. Oderaotoshi, S. Minakata, M. Komatsu, J. Am. Chem. Soc. 2002, 124, 3812;
68. e) T. Ishiyama, S. Abe, N. Miyaura, A. Suzuki, Chem. Lett. 1992, 21, 691;
69. f) G. Manolikakes, P. Knochel, Angew. Chem. Int. Ed. 2009, 48, 205;
70. Angew. Chem. 2009, 121, 211;
71. g) H. Liu, Z. Qiao, X. Jiang, Org. Biomol. Chem. 2012, 10, 7274;
72. h) S. Sumino, A. Fusano, T. Fukuyama, I. Ryu, Acc. Chem. Res. 2014, 47, 1563;
73. i) B. M. Monks, S. P. Cook, Angew. Chem. Int. Ed. 2013, 52, 14214;
74. Angew. Chem. 2013, 125, 14464;
75. j) S. Bräse, B. Waegell, A. de Meijere, Synthesis 1998, 148.
76. Early mechanistic studies: A. V. Kramer, J. A. Osborn, J. Am. Chem. Soc. 1974, 96, 7832.