Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination

Angewandte Chemie - International Edition

Volumn 49, Issue 35, 2010, Pages 6169-6173

  Engle, Keary M ^a   Wang, Dong Hui ^a   Yu, Jin Quan ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Arenes; Aromatic substitution; C H activation; Olefination; Palladium

Indexed keywords

ARENES; AROMATIC SUBSTITUTIONS; C-H ACTIVATION; C-H FUNCTIONALIZATION; CATALYTIC SYSTEM; OLEFINATION;

ACTIVATION ANALYSIS; CATALYSIS; FUNCTIONAL GROUPS; PALLADIUM; PALLADIUM COMPOUNDS;

AROMATIC COMPOUNDS;

ALKENE; CARBON; HYDROGEN; PALLADIUM; STYRENE;

CATALYSIS; CHEMISTRY; SYNTHESIS;

ALKENES; CARBON; CATALYSIS; HYDROGEN; PALLADIUM; STYRENE;

EID: 77956050659     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002077     Document Type: Article

References (81)

1. J.H. Burroughes, D. D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, Nature 1990, 347, 539.
2. For reviews of electroluminescent conjugated polymers, see: a) A. Kraft, A.C. Grimsdale, A.B. Holmes, Angew. Chem. 1998, 110, 416;
3. Angew. Chem. Int. Ed. 1998, 37, 402;
4. A.C. Grimsdale, K.L. Chan, R.E. Martin, P.G. Jokisz, A. B Holmes, Chem. Rev. 2009, 109, 897.
5. T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581;
6. R.F. Heck, J.P. Nolley, Jr., J. Org. Chem. 1972, 37, 2320.
7. J.E. Plevyak, R.F. Heck, J. Org. Chem. 1978, 43, 2454.
8. For examples of differential Mizoroki-Heck reactions to construct unsymmetrical divinylbenzenes, see: a) J.E. Plevyak, J.E. Dickerson, R.F. Heck, J. Org. Chem. 1979, 44, 4078;
9. A.J. Spencer, J. Organomet. Chem. 1984, 265, 323;
10. W.-J. Tao, S. Nesbitt, R.F. Heck, J. Org. Chem. 1990, 55, 63;
11. A.-S. Carlström, T. Frejd, J. Org. Chem. 1991, 56, 1289;
12. S. Sengupta, S.K. Sadhukhan, Tetrahedron Lett. 1998, 39, 715;
13. C.Wang, L.- S. Tan, J.-P. He, H.-W. Hu, J.-H. Xu, Synth. Commun. 2003, 33, 773.
14. For examples of differential cross-coupling reactions, see: a) T. Oh-e, N. Miyaura, A. Suzuki, Synlett 1990, 221;
15. Rottländer M., Palmer N., Knochel P., Synlett, 1996, 573.
16. For reviews, see: a) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633;
17. L.-C. Campeau, D.R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35;
18. X. Chen, K.M. Engle, D.-H Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196;
19. Angew. Chem. Int. Ed. 2009, 48, 5094;
20. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074;
21. T.W. Lyons, M.S. Sanford, Chem. Rev. 2010, 110, 1147.
22. -H olefination, see: a) I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119.
23. For selected examples of subsequent work to establish catalytic turnover and expand the substrate scope, see: a) Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166;
24. R. Shue, J. Chem. Soc. D 1971, 1510;
25. Y. Fujiwara, R. Asano, I. Moritani, S. Teranishi, J. Org. Chem. 1976, 41, 1681;
26. J. Tsuji, H. Nagashima, Tetrahedron 1984, 40, 2699;
27. C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097;
28. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992.
29. II-catalyzed C-H olefination with nitrogen-containing heterocycles, see: a) Y. Fujiwara, O. Maruyama, M. Yoshidomi, H. Taniguchi, J. Org. Chem. 1981, 46, 851;
30. T. Itahara, M. Ikeda, T. Sakakibara, J. Chem. Soc. Perkin Trans. 1 1983, 1361;
31. E.M. Ferreira, B.M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578;
32. G. Abbiati, E.M. Beccalli, G. Broggini, C. Zoni, J. Org. Chem. 2003, 68, 7625;
33. S. Ma, S. Yu, Tetrahedron Lett. 2004, 45, 8419;
34. C. Liu, R.A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 10250;
35. N.P. Grimster, C. Gauntlett, C. R.A. Godfrey, M.J. Gaunt, Angew. Chem. 2005, 117, 3185;
36. Angew. Chem. Int. Ed. 2005, 44, 3125.
37. II-catalyzed C-H olefination using substrates containing directing groups, see: a) M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211;
38. M.D.K. Boele, G. P.F. van Strijdonck, A.H.M. de Vries, P. C.J. Kamer, J.G. de Vries, P.W. N.M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586;
39. V.G. Zaitsev, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 4156;
40. G. Cai, Y. Fu, Y. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 7666;
41. C.E. Houlden, C.D. Bailey, J.G. Ford, M.R. Gagné, G.C. Lloyd-Jones, K.I. Booker- Milburn, J. Am. Chem. Soc. 2008, 130, 10066;
42. J.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. 2008, 120, 6552;
43. Angew. Chem. Int. Ed. 2008, 47, 6452;
44. Y. Lu, D.-H. Wang, K.M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916.
45. E. Capito, J.M. Brown, A. Ricci, Chem. Commun. 2005, 1854;
46. A. García-Rubia, R.G. Arrayás, J.C. Carretero, Angew. Chem. 2009, 121, 6633;
47. Angew. Chem. Int. Ed. 2009, 48, 6511.
48. S.H. Cho, S.J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254.
49. D.-H. Wang, K.M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315.
50. II-catalyzed C-H olefination with electron-deficient arenes, see: Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072.
51. II-mediated C-H olefination in total synthesis, see: a) B.M. Trost, S.A. Godleski, J.P. Genêt, J. Am. Chem. Soc. 1978, 100, 3930;
52. T.D. Cushing, J.F. Sanz-Cervera, R. M.Williams, J. Am. Chem. Soc. 1993, 115, 9323;
53. P.S. Baran, E.J. Corey, J. Am. Chem. Soc. 2002, 124, 7904;
54. N.K. Garg, D.D. Caspi, B.M. Stoltz, J. Am. Chem. Soc. 2004, 126, 9552;
55. Beck E.M., Hatley R., Gaunt M.J., Angew. Chem., 2008, 120, 3046.
56. E.M. Beck, R. Hatley, M.J. Gaunt, Angew. Chem. 2008, 120, 3046; Angew. Chem. Int. Ed. 2008, 47, 3004;
57. A.L. Bowie, Jr., D. Trauner, J. Org. Chem. 2009, 74, 1581.
58. For examples of arene-olefin coupling reactions using metals other than Pd, see: a) L.N. Lewis, J.F. Smith, J. Am. Chem. Soc. 1986, 108, 2728;
59. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529;
60. T. Matsubara, N. Koga, D.G. Musaev, K. Morokuma, J. Am. Chem. Soc. 1998, 120, 12692;
61. C.P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1999, 121, 6616;
62. T. Matsumoto, D.J. Taube, R.A. Periana, H. Taube, H. Yoshida, J. Am. Chem. Soc. 2000, 122, 7414;
63. C.-H. Jun, J.-B. Hong, Y.-H. Kim, Y.-H. Chung, Angew. Chem. 2000, 112, 3582;
64. Angew. Chem. Int. Ed. 2000, 39, 3440;
65. H. Weissman, X. Song, D. Milstein, J. Am. Chem. Soc. 2001, 123, 337;
66. R.K. Thalji, J.A. Ellman, R.G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192;
67. A.T. Luedtke, K.I. Goldberg, Angew. Chem. 2008, 120, 7808;
68. Angew. Chem. Int. Ed. 2008, 47, 7694.
69. For a novel approach to construct 1,2,3-trisubstituted arenes through norbornene-mediated Pd0 catalysis, see: a) M. Catellani, G.P. Chiusoli, J. Organomet. Chem. 1988, 346, C27;
70. M. Catellani, F. Frignani, A. Rangoni, Angew. Chem. 1997, 109, 142;
71. Angew. Chem. Int. Ed. Engl. 1997, 36, 119.
72. For a review, see: c) D. Alberico, M.E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174. For recent work, see:
73. B. Mariampillai, J. Alliot, M. Li, M. Lautens, J. Am. Chem. Soc. 2007, 129, 15372;
74. K.M. Gericke, D.I. Chai, N. Bieler, M. Lautens, Angew. Chem. 2009, 121, 1475;
75. Angew. Chem. Int. Ed. 2009, 48, 1447.
76. For rare examples of sequential C-H activation of electron-rich heterocycles with PdII, see Refs. [10g,12b, 16e] and the following: a) M. Nakano, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1851;
77. S. Yanagisawa, K. Ueda, H. Sekizaawa, K. Itami, J. Am. Chem. Soc. 2009, 131, 14622.
78. For a recent example of sequential ortho-C-H olefination of 1- phenylpyrazoles using catalytic RhIII, see: N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7094.
79. IIcatalyzed enantioselective C-Hactivation reactions, see: a) B.-F. Shi, N. Maugel, Y.-H. Zhang, J.-Q. Yu, Angew. Chem. 2008, 120, 4960;
80. Angew. Chem. Int. Ed. 2008, 47, 4882;
81. B.-F. Shi, Y.-H. Zhang, J.K. Lam, D.-H.Wang, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 460.