Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium-arylurea complexes

Tetrahedron

Volumn 69, Issue 47, 2013, Pages 10139-10151

  Smith, Matthew R ^a   Jang, Young Jin ^a   Kim, Jung Yun ^a   Ciufolini, Marco A ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Arylation; Arylureas; Heck reaction; Ligands; Palladium

Indexed keywords

ALDEHYDE; ALKENE; ESTER; IODIDE; KETONE; NITRILE; PALLADIUM; UREA;

ARTICLE; ARYLATION; ELECTRON; HECK ARYLATION; PRIORITY JOURNAL;

EID: 84885953914     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.09.019     Document Type: Article

References (88)

1. M.R. Smith, J.Y. Kim, and M.A. Ciufolini Tetrahedron Lett. 54 2013 2042 2045
2. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem. 37 1972 2320 2322 Reviews
3. R.F. Heck Org. React. 27 1989 345 390
4. I. Beletskaya, and A. Cheprakov Chem. Rev. 100 2000 3009 3066
5. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4221
6. S. Bräse, and A. de Meijere F. Diederich, P.J. Stang, Metal-catalyzed Cross-coupling Reactions 2nd ed. 2004 Wiley-VCH Weinheim, Germany 217 316
7. X. Cui, Y. Zhou, N. Wang, L. Liu, and Q.X. Guo Tetrahedron Lett. 48 2007 163 167
8. X. Cui, J. Li, Y. Fu, L. Liu, and Q.X. Guo Tetrahedron Lett. 49 2008 3458 3462
9. H. Liang, Y. Zhou, and M.A. Ciufolini Synthesis 2010 2515 2520
10. T.E. Barder, S.D. Walker, J.R. Martinelli, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 4685 4696
11. Review: R. Chinchilla, and C. Najera Chem. Soc. Rev. 40 2011 5084 5121
12. E. Colacino, J. Martinez, and F. Lamaty J. Cossy, S. Arseniyadis, Modern Tools for the Synthesis of Complex Bioactive Molecules 2012 John Wiley & Sons Hoboken, NJ 33
13. J.G. de Vries Top. Organomet. Chem. 42 2012 1 34
14. J. Gomez-Catalan, J.J. Perez, A.I. Jimenez, and C. Cativiela J. Pept. Sci. 5 1999 251 262
15. B.E. Haug, M.L. Skar, and J.S. Svendsen J. Pept. Sci. 7 2001 425 432
16. B.-K. Cho, J.-H. Seo, T.-J. Kang, J. Kim, H.-Y. Park, B.-S. Lee, and B.-G. Kim Biotechnol. Bioeng. 94 2006 842 850
17. H. Josien, S. Lavielle, A. Brunissen, M. Saffroy, Y. Torrens, J.-C. Beaujouan, J. Glowinski, and G. Chassaing J. Med. Chem. 37 1994 1586 1601
18. C.E. Augelli-Szafran, B.D. Roth, A. Essenburg, K.L. Hamelehle, B.R. Krause, and R.L. Stanfield Bioorg. Med. Chem. Lett. 4 1994 1095 1100
19. B.J. Williams, M. Teall, J. Kenna, T. Harrison, C.J. Swain, M.A. Cascieri, S. Sadowski, C. Strader, and R. Baker Bioorg. Med. Chem. Lett. 16 1994 1903 1908
20. M.C. Pavar, K. Hanif, A. Azam, S. Lata, M.A. Qadar Pasha, and S. Pasha Bioorg. Med. Chem. Lett. 16 2006 2117 2121
21. B.R. Stranix, J.-F. Lavallee, G. Sevigny, J. Yelle, V. Perron, N. LeBerre, D. Herbart, and J.J. Wu Bioorg. Med. Chem. Lett. 16 2006 3459 3562
22. M. Pippel, B.D. Allison, V.K. Phuong, L. Li, M.F. Morton, C. Prendergast, X. Wu, N.P. Shankley, and M.H. Rabinowitz Bioorg. Med. Chem. Lett. 19 2009 6373 6375
23. A. Murza, A. Parent, E. Besserer-Offroy, H. Tremblay, F. Karadereye, N. Beaudet, R. Leduc, P. Sarret, and E. Marsault Chem. Med. Chem. 7 2012 318 325
24. D.E. Patterson, S. Xie, L.A. Jones, M.H. Osterhout, C.G. Henry, and T.D. Roper Org. Process Res. Dev. 11 2007 624 627
25. D.E. Patterson, J.D. Powers, M. LeBlanc, T. Sharkey, E. Boehler, E. Irdam, and M.H. Osterhout Org. Process Res. Dev. 13 2009 900 906
26. D.E. Patterson, S. Xie, L.A. Jones, M.H. Osterhout, C.G. Henry, and T.D. Roper H.U. Blaser, H.J. Federsel, Asymmetric Catalysis on Industrial Scale 2nd ed. 2010 Wiley-VCH Weinheim, Germany 473 484
27. G. Deng, D. Ye, Y. Li, L. He, Y. Zhou, J. Wang, J. Li, H. Jiang, and H. Liu Tetrahedron 64 2008 10512 10516
28. V.A. Soloshonok, and T. Ono J. Fluorine Chem. 130 2009 547 549
29. D.A. Evans, T.C. Britton, R.L. Dorow, and J.F. Dellaria Jr. Tetrahedron 44 1988 5525 5540
30. D.A. Evans, T.C. Britton, J.A. Ellman, and R.L. Dorow J. Am. Chem. Soc. 112 1990 4011 4030
31. J. Lin, S. Liao, and V.J. Hruby Tetrahedron Lett. 39 1998 3117 3120
32. J. Lin, S. Liao, and V.J. Hruby J. Peptide Res. 65 2005 105 112
33. E.g.: M. Moreno-Manas, M. Perez, and R. Pleixat Tetrahedron Lett. 37 1996 7449 7452
34. T. Ikemoto, T. Nagata, M. Yamano, T. Ito, Y. Mizuno, and K. Tomimatsu Tetrahedron Lett. 45 2004 7757 7760
35. L. Botella, and C. Najera J. Org. Chem. 70 2005 4360 4369
36. A.F. Littke, and G.C. Fu J. Am. Chem. Soc. 123 2001 6989 7000
37. I. Kondolff, H. Doucet, and M. Santelli Tetrahedron Lett. 44 2003 8487 8491
38. B.H. Allam, and K.N. Singh Synthesis 2011 1125 1131
39. E. Mieczynska, A. Gniewek, I. Pryjomska-Ray, A.M. Trzeciak, H. Grabowska, and M. Zawadski Appl. Cat. A: Gen. 393 2011 195 205
40. C. Guertler, and S.L. Buchwald Chem. - Eur. J. 5 1999 3107 3112
41. S. Cacchi, F. Gasparrini, P. Pace, and C. Villani Synlett 2000 650 652
42. H. Naito, S. Ohsuki, M. Sugimori, R. Atsumi, M. Minami, Y. Nakamura, M. Ishii, K. Hirotani, E. Kumazawa, and A. Ejima Chem. Pharm. Bull. 50 2002 453 462
43. U.S. Sorensen, T.J. Bleisch, A.E. Kingston, R.A. Wright, B.G. Johnson, D.D. Schoepp, and P.L. Ornstein Bioorg. Med. Chem. 11 2003 197 205
44. A. Minatti, X. Zheng, and S.L. Buchwald J. Org. Chem. 72 2007 9253 9258
45. Y. Fall, H. Doucet, and M. Santelli Tetrahedron 65 2009 489 495 and literature cited therein
46. A. Nejjar, C. Pinel, and L. Djakovitch Adv. Synth. Catal. 345 2003 612 619
47. V.K. Aggarwal, A.C. Staubitz, and M. Owen Org. Process Res. Dev. 10 2006 64 69
48. M. Stadler, and B. List Synlett 2008 597 599
49. C.F.B. Praquin, P.D. de Koning, P.J. Peach, R.M. Howard, and S.L. Spencer Org. Process Res. Dev. 15 2011 1124 1129
50. K. Yamazaki, Y. Nakamura, and Y. Kondo J. Org. Chem. 68 2003 6011 6019
51. S.E. Gibson, and R.J. Middleton J. Chem. Soc., Chem. Commun. 1995 1743 1744
52. 2, mixtures of products). Recent work
53. A.L. Gottumukkala, J.G. de Vries, and A.J. Minnaard Chem. - Eur. J. 17 2011 3091 3095 (1.5 mol % Pd(0)-NHC ligands, ca. 80% yield)
54. The first example of such double arylation reactions was reported by Heck himself: R.F. Heck Acc. Chem. Res. 12 1979 146 151 and references cited therein
55. M.T. Reetz, R. Breinbauer, and K. Wanninger Tetrahedron Lett. 37 1996 4499 4502
56. Y. Li, X.M. Hong, D.M. Collard, and M.A. El-Sayed Org. Lett. 2 2000 2385 2388
57. M. Moreno-Manas, R. Pleixats, and S. Villaroya Organometallics 20 2001 4524 4528
58. M. Shakeri, C.-W. Tai, E. Gothelid, S. Oscarsson, and J.-E. Backvall Chem. - Eur. J. 17 2011 13269 13273
59. N.T.S. Phan, M. Van Der Sluys, and C.W. Jones Adv. Synth. Catal. 348 2006 609 679
60. L. Djakovitch, K. Köhler, and J.G. de Vries D. Astruc, Nanoparticles and Catalysis 2008 Wiley-VCH New York, NY 303 ff
61. V.F. Slagt, A.H.M. de Vries, J.G. de Vries, and R.M. Kellogg Org. Process Res. Dev. 14 2010 30 47
62. E. Ye, H. Tan, S. Li, and W.Y. Fan Angew. Chem., Int. Ed. 45 2006 1120 1123
63. M.T. Reetz, and J.G. de Vries Chem. Commun. 2004 1559 1563
64. A. Alimardanov, L. Schmieder-van de Vondervoort, A.H.M. de Vries, and J.G. de Vries Adv. Synth. Catal. 346 2004 1812 1817
65. Cf A.D. Benavidez, L. Kovarik, A. Genc, N. Agrawal, E.M. Larsson, T.W. Hansen, A.M. Karim, and A.K. Datye ACS Catal. 2 2012 2349 2356
66. A.Y. Stakheev, I.S. Mashkovskii, G.N. Baeva, and N.S. Telegina Russ. J. Gen. Chem. 80 2010 618 629
67. U. Christmann, and R. Vilar Angew. Chem., Int. Ed. 44 2005 366 374
68. T. Yamamoto, M. Nishiyama, and Y. Koie Tetrahedron Lett. 39 1998 2367 2370
69. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 37 1998 3387 3388
70. Known compound: H. Lorenz Helv. Chem. Acta 28 1945 600 612
71. Known compound: I.A. Poletaeva, and O.F. Ginzburg Russ. J. Org. Chem. 4 1968 440 442
72. Known compound: C. Ebner, and A. Pfaltz Tetrahedron 67 2011 10287 10290
73. Known compound: G. Singh, M.L. Purkayastha, H. Ha, and H. Junjappa J. Chem. Soc., Perkin Trans. 1 1985 1289 1294
74. Known compound: T. Ohmura Synlett 2008 423 427
75. Known compound: D. Yang, Y.-C. Chen, and N.-Y. Zhu Org. Lett. 6 2004 1577 1580
76. Known compound: D.-H. Lee, A. Taher, S. Hossain, and M.-J. Jin Org. Lett. 13 2011 1432 1435
77. Known compound: C. Qin, and N. Jiao J. Am. Chem. Soc. 132 2010 15893 15895
78. Known compound: J. Takaya, K. Sasano, and N. Iwasawa Org. Lett. 13 2011 1698 1701
79. Known compound: A.L. Gottumukkala, J.F. Teichert, D. Heijnen, N. Eisink, S. van Dijk, C. Ferrer, A. van den Hoogenband, and A.J. Minnaard J. Org. Chem. 76 2011 3498 3501
80. Known compound: M. Uyanik, R. Fukatsu, and K. Ishihara Org. Lett. 11 2009 3470 3473
81. Known compound: G.V. Kryshtal Eur. J. Org. Chem. 13 2005 2822 2827
82. Known compound: F.W. Ullrich Synthesis 1983 641 645
83. Known compound: R.W. Guthrie, G.L. Kaplan, F.A. Mennona, J.W. Tilley, R.W. Kierstead, J.G. Mullin, R.A. LeMahieu, S. Zawoiski, and M. O'Donnell J. Med. Chem. 32 1989 1820 1835
84. Known compound: E. Tullberg, D. Peters, and T. Frejd J. Organomet. Chem. 689 2004 3778 3781
85. Known compound: M. Kometani, K. Ihara, R. Kimura, and H. Kinoshita Bull. Chem. Soc. Jpn. 82 2009 364 380
86. A. Cieplak, B.D. Tait, and C.R. Johnson J. Am. Chem. Soc. 111 1989 8447 8462
87. Known compound: K.-F. Chen Org. Lett. 11 2009 377 380
88. Known compound: A.L. Gottumukkala Chem. - Eur. J. 17 2011 3091 3095