Pd-arylurea complexes for the Heck arylation of crotonic and cinnamic substrates

Tetrahedron Letters

Volumn 54, Issue 16, 2013, Pages 2042-2045

  Smith, Matthew R ^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; CINNAMIC ACID; ESTER; IODINE DERIVATIVE; KETONE; LEAD; NITRILE; UREA DERIVATIVE;

ARTICLE; ARYLATION; CATALYST; CHEMICAL STRUCTURE; ELECTRON; HECK REACTION;

EID: 84875208906     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.077     Document Type: Article

References (50)

1. X. Cui, Y. Zhou, N. Wang, L. Liu, and Q.X. Guo Tetrahedron Lett. 48 2007 163 167
2. X. Cui, J. Li, Y. Fu, L. Liu, and Q.X. Guo Tetrahedron Lett. 49 2008 3458 3462
3. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem. 37 1972 2320 2322
4. Reviews R.F. Heck Org. React. 27 1989 345 390
5. I. Beletskaya, and A. Cheprakov Chem. Rev. 100 2000 3009 3066
6. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4221
7. 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
8. Review N. Miyaura, and N. Suzuki Chem. Rev. 95 1995 2457 2483
9. T.E. Barder, S.D. Walker, J.R. Martinelli, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 4685 4696
10. H. Liang, Y. Zhou, and M.A. Ciufolini Synthesis 2010 2515 2520
11. J. Gomez-Catalan, J.J. Perez, A.I. Jimenez, and C. Cativiela J. Pept. Sci. 5 1999 251 262
12. B.E. Haug, M.L. Skar, and J.S. Svendsen J. Pept. Sci. 7 2001 425 432
13. 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
14. 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
15. 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
16. 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
17. M.C. Pavar, K. Hanif, A. Azam, S. Lata, M.A. Qadar Pasha, and S. Pasha, Bioorg. Med. Chem. Lett. 16 2006 2117 2121
18. 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
19. 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
20. A. Murza, A. Parent, E. Besserer-Offroy, H. Tremblay, F. Karadereye, N. Beaudet, R. Leduc, P. Sarret, and E. Marsault ChemMedChem 7 2012 318 325
21. D.E. Patterson, S. Xie, L.A. Jones, M.H. Osterhout, C.G. Henry, and T.D. Roper Org. Proc. Res. Dev. 11 2007 624 627
22. D.E. Patterson, J.D. Powers, M. LeBlanc, T. Sharkey, E. Boehler, E. Irdam, and M.H. Osterhout Org. Proc. Res. Dev. 13 2009 900 906
23. 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
24. See also G. Deng, D. Ye, Y. Li, L. He, Y. Zhou, J. Wang, J. Li, H. Jiang, and H. Liu Tetrahedron 64 2008 10512 10516
25. V.A. Soloshonok, and T. Ono J. Fluorine Chem. 130 2009 547 549
26. D.A. Evans, T.C. Britton, R.L. Dorow, and J.F. Dellaria Jr. Tetrahedron 44 1988 5525 5540
27. D.A. Evans, T.C. Britton, J.A. Ellman, and R.L. Dorow J. Am. Chem. Soc. 112 1990 4011 4030
28. J. Lin, S. Liao, and V.J. Hruby Tetrahedron Lett. 39 1998 3117 3120
29. J. Lin, S. Liao, and V.J. Hruby J. Pept. Res. 65 2005 105 112
30. L.H. Klemm, and G.M. Bower J. Org. Chem. 23 1958 344 348
31. E.g. T. Ikemoto, T. Nagata, M. Yamano, T. Ito, Y. Mizuno, and K. Tomimatsu Tetrahedron Lett. 45 2004 7757 7760
32. M. Moreno-Manas, M. Perez, and R. Pleixat Tetrahedron Lett. 37 1996 7449 7452 See also Refs. 15-20
33. L. Botella, and C. Najera J. Org. Chem. 70 2005 4360 4369 and literature cited therein. See also bibliography in Ref. 14
34. A.F. Littke, and G.C. Fu J. Am. Chem. Soc. 123 2001 6989 7000
35. I. Kondolff, H. Doucet, and M. Santelli Tetrahedron Lett. 44 2003 8487 8491
36. B.H. Allam, and K.N. Singh Synthesis 2011 1125 1131
37. E. Mieczynska, A. Gniewek, I. Pryjomska-Ray, A.M. Trzeciak, H. Grabowska, and M. Zawadski Appl. Cat., A: Gen. 393 2011 195 205
38. C. Guertler, and S.L. Buchwald Chem. Eur. J. 5 1999 3107 3112
39. J.-Z. Jiang, and C. Cai J. Disp. Sci. Tech. 27 2006 1137 1140
40. Recent work S. Cacchi, F. Gasparrini, P. Pace, and C. Villani Synlett 2000 650 652
41. 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
42. 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
43. A. Minatti, A. Minatti, X. Zheng, and S.L. Buchwald J. Org. Chem. 72 2007 9253 9258
44. Y. Fall, H. Doucet, and M. Santelli Tetrahedron 65 2009 489 495 and literature cited therein
45. A. Nejjar, C. Pinel, and L. Djakovitch Adv. Synth. Catal. 345 2003 612 619
46. V.K. Aggarwal, A.C. Staubitz, and M. Owen Org. Proc. Res. Dev. 10 2006 64 69
47. M. Stadler, and B. List Synlett 2008 597 599
48. 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)
49. 2, mixtures of products)
50. Details are provided as Supplementary data.