[Pd(PPh3)2 (saccharinate)2]- general catalyst for Suzuki-Miyaura, Negishi cross-coupling and C-H bond functionalization of coumaryl and pyrone substrates

Tetrahedron

Volumn 69, Issue 5, 2013, Pages 1446-1453

  Shah, Parin ^a   Santana, M Dolores ^b   García, Joaquín ^b   Serrano, J Luis ^c   Naik, Minal ^d   Pednekar, Suhas ^d   Kapdi, Anant R ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b UNIVERSITY OF MURCIA   (Spain)

^c TECHNICAL UNIVERSITY OF CARTAGENA   (Spain)

^d RAMNARAIN RUIA COLLEGE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

[PALLADIUM(TRIPHENYLPHOSPHINE) 2(SACCHARINATE)2]; BORONIC ACID DERIVATIVE; COUMARIN DERIVATIVE; PALLADIUM COMPLEX; PYRONE DERIVATIVE; SACCHARIN SODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; COVALENT BOND; DRUG STRUCTURE; DRUG SYNTHESIS; NEGISHI CROSS COUPLING; PRIORITY JOURNAL; REACTION TIME; SUZUKI REACTION;

EID: 84872106352     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.12.030     Document Type: Article

References (70)

1. A. Murakami, G. Gao, M. Omura, M. Yano, C. Ito, H. Furukawa, D. Takahashi, K. Koshimizu, and H. Ohigashi Bioorg. Med. Chem. Lett. 10 2000 59
2. W. Maier, J. Schmidt, M. Nimtz, V. Wray, and D. Strack Phytochemistry 54 2000 473
3. A.N. Garcia-Argaez, T.A. Ramirez Apan, H.A. Delgado, G. Velazquez, and M. Martinez-Vazquez Planta Med. 66 2000 279
4. P. Zhou, Y. Takaishi, H. Duan, B. Chen, G. Honda, M. Itoh, Y. Takeda, O.K. Kodzhimatov, and K.H. Lee Phytochemistry 53 2000 689
5. M. Gellert, M.H. O'Dea, T. Itoh, and J.I. Tomizawa Proc. Natl. Acad. Sci. U.S.A. 73 1976 4474
6. R.D.H. Murray, J. Mendez, and S.A. Brown The Natural Coumarins: Occurrence, Chemistry, and Biochemistry 1982 Wiley New York, NY
7. T. Hatano, T. Yasuhara, T. Fukuda, T. Noro, and T. Okuda Chem. Pharm. Bull. 37 1989 3005
8. J.A. Ali, A.P. Jackson, A.J. Howells, and A. Maxwell Biochemistry 32 1993 2717
9. N.A. Pereira, B.M.R. Pereira, M.C. do Nascimento, J.P. Parente, and W.B. Mors Planta Med. 60 1994 99
10. B. Naser-Hijazi, B. Stolze, and K.S. Zanker Second Proceedings of The International Society of Coumarin Investigators 1994 Springer Berlin
11. D.M.X. Donnelly, and M.H. Sheridan J.B. Harborne, The Flavonoids, Advances in Research Since 1980 1988 Chapman and Hall London 211 232
12. O.A. Akrawi, G.Z. Nagy, T. Patonay, A. Villinger, and P. Langer Tetrahedron Lett. 53 2012 3206 and references therein
13. For coumarins see: L.C.C. Vieira, M.W. Paixao, and A.G. Corrêa Tetrahedron Lett. 53 2012 2715
14. H. Sakai, T. Hirano, S. Mori, S. Fujii, H. Masuno, M. Kinoshita, H. Kagechika, and A. Tanatani J. Med. Chem. 54 2011 7055
15. M. Schiedel, C. Briehn, and P. Baüerle J. Organomet. Chem. 653 2002 200
16. N.S. Sitnikov, A.S. Shavyrin, G.K. Fukin, I.P. Beletskaya, S. Combes, and A.Y. Fedorova Russ. Chem. B 59 2010 626
17. M.J.R.P. Queiroz, A.S. Abreu, R.C. Calhelha, M.S.D. Carvalho, and P.M.T. Ferreira Tetrahedron 64 2008 5139
18. S. Hesse, and G. Kirsch Tetrahedron Lett. 43 2002 1213
19. W. Gao, Y. Luo, Q. Ding, Y. Peng, and J. Wua Tetrahedron Lett. 51 2010 136
20. M.J. Matos, S. Vazquez-Rodriguez, F. Borges, L. Santana, and E. Uriarte Tetrahedron Lett. 52 2011 1225
21. L.R. Marrison, J.M. Dickinson, R. Ahmed, and I.J.S. Fairlamb Tetrahedron Lett. 43 2002 8853
22. I.J.S. Fairlamb, S.M. Syvanne, and A.C. Whitwood Synlett 2003 1691
23. L.R. Marrison, J.M. Dickinson, and I.J.S. Fairlamb Bioorg. Med. Chem. Lett. 12 2002 3509
24. I.J.S. Fairlamb, F.J. Lu, J.P. Schmidt, L.R. Marrison, and J.M. Dickinson Bioorg. Med. Chem. 12 2004 4285
25. Y.B. Kwon, J. Park, B.R. Choi, H.S. Kim, and Ch. M. Yoon Bull. Korean Chem. Soc. 32 2011 2897
26. Ch. R. Reddy, B. Srikanth, N.N. Rao, and D.-R. Shin Tetrahedron 64 2008 11666
27. A.O. King, N. Okukado, and E. Negishi J. Chem. Soc., Chem. Commun. 1977 683
28. A.O. King, and E. Negishi J. Org. Chem. 43 1978 358
29. E. Negishi, K. Akiyashi, and T. Takahashi J. Chem. Soc., Chem. Commun. 1987 477
30. E. Negishi Acc. Chem. Res. 15 1982 340
31. E. Negishi H. Nozaki, Current Trends in Organic Synthesis 1983 Pergamon Oxford 269
32. E. Negishi, and F. Liu F. Diederich, P.J. Stang, Metal-Catalyzed Cross-Coupling Reactions 1998 VCH Weinheim 1 47
33. E. Negishi, Q. Hu, Z. Huang, X. Qian, and G. Wang Aldrichimica Acta 38 2005 71
34. J. Wu, and Z. Yang J. Org. Chem. 66 2001 7875
35. J. Wu, Y. Liao, and Z. Yang J. Org. Chem. 66 2001 3642
36. I.J.S. Fairlamb, A.R. Kapdi, J.M. Lynam, R.J.K. Taylor, and A.C. Whitwood Tetrahedron 60 2004 5711
37. N.M. Chaignon, I.J.S. Fairlamb, A.R. Kapdi, R.J.K. Taylor, and A.C. Whitwood J. Mol. Catal. A: Chem. 219 2004 191
38. I.J.S. Fairlamb, R.J.K. Taylor, J.L. Serrano, and G. Sanchez New J. Chem. 30 2006 1695
39. C.M. Crawforth, S. Burling, I.J.S. Fairlamb, R.J.K. Taylor, and A.C. Whitwood Chem. Commun. 2003 2194
40. C.M. Crawforth, I.J.S. Fairlamb, and R.J.K. Taylor Tetrahedron Lett. 45 2004 461
41. C.M. Crawforth, S. Burling, I.J.S. Fairlamb, A.R. Kapdi, and R.J.K. Taylor Tetrahedron 61 2005 9736
42. M.J. Burns, I.J.S. Fairlamb, A.R. Kapdi, P. Sehnal, and R.J.K. Taylor Org. Lett. 9 2007 5397
43. J.L. Serrano, I.J.S. Fairlamb, G. Sanchez, L. Garca, J. Perez, J. Vives, G. Lopez, C.M. Crawforth, and R.J.K. Taylor Eur. J. Inorg. Chem. 2004 2706
44. I.J.S. Fairlamb, A.R. Kapdi, A.F. Lee, G. Sanchez, G. Lopez, J.L. Serrano, J. Garca, J. Perez, and E. Perez Dalton Trans. 2004 3970
45. C.M. Crawforth, S. Burling, I.J.S. Fairlamb, A.R. Kapdi, R.J.K. Taylor, J.L. Serrano, and G. Sanchez Adv. Synth. Catal. 348 2006 405
46. H. Adams, N. Bailey, T.N. Briggs, J.N. McCleverty, H.M. Colquhoun, and D.G. Williams J. Chem. Soc., Dalton Trans. 1986 813
47. G. Sánchez, J. García, M. Martínez, J. Pérez, L. García, J.L. Serrano, and A.R. Kapdi Dalton Trans. 40 2011 12676
48. M.D. Santana, R. García-Bueno, G. García, G. Sánchez, J. García, M. Naik, S. Pednekar, A.R. Kapdi, J. Pérez, L. García, E. Pérez, and J.L. Serrano Dalton Trans. 41 2012 3832
49. M.J. Burns, R.J. Thatcher, R.J.K. Taylor, and I.J.S. Fairlamb Dalton Trans. 39 2010 10391
50. L. Tang, Y. Pang, Q. Yan, L. Shi, J. Huang, Y. Du, and K. Zhao J. Org. Chem. 76 2011 2744
51. L. Schio, F. Chatreaux, and M. Klich Tetrahedron Lett. 41 2000 1543
52. J. Wu, L. Wang, R. Fathi, and Z. Yang Tetrahedron Lett. 43 2002 4395
53. X. Fu, S. Zhang, J. Yin, and D.J. Schumacher Tetrahedron Lett. 43 2002 6673
54. Z.Y. Tang, and Q.S. Hu Adv. Synth. Catal. 346 2004 1635
55. A.L. Hansen, and T. Skrysdstrup Org. Lett. 7 2005 5585
56. V. Percec, J.Y. Bae, and H.D. Hill J. Org. Chem. 60 1995 1060
57. E. Kobayashi, and R. Mizojiri Tetrahedron Lett. 37 1996 8531
58. D. Zim, V.R. Lando, J. Dupont, and A.L. Monteiro Org. Lett. 3 2001 3049
59. For ruthenium-catalyzed Suzuki-Miyaura cross coupling of 4-coumaryl tosylates see: J. Wu, L. Zhang, and Y. Luo Tetrahedron Lett. 47 2006 6747
60. Y. Luo, and J. Wu Tetrahedron Lett. 50 2009 2103
61. M. Catellani, G.P. Chiusoli, M.C. Fagnola, and G. Solari Tetrahedron Lett. 35 1994 5919
62. M.L.N. Rao, V. Venkatesh, and D.N. Jadhav Eur. J. Org. Chem. 20 2010 3945
63. G. Roma, D. Piras, M. Di Braccio, and G. Grossi Synthesis 5 2010 849
64. J.I. Kuroda, K. Inamoto, K. Hiroya, and T. Doi Eur. J. Org. Chem. 14 2009 2251
65. Y. Li, Z. Qi, H. Wang, X. Fu, and C. Duan J. Org. Chem. 77 2012 2053
66. P.Y. Wong, W.K. Chow, K.H. Chung, C.M. So, C.P. Lau, and F.Y. Kwong Chem. Commun. 2011 8328
67. V.N. Kalinin, O.S. Shilova, D.S. Okladnoi, and H. Schmidhammer Doklady Chem. 351 1996 276
68. J. Tonannavar, J. Yenagi, V. Sortur, V.B. Jadhav, and M.V. Kulkarni Spectrochim. Acta, Part A: Mol. Biomol. Spec. 77 2010 351
69. H. Cao, and W.-J. Xiao Can. J. Chem. 83 2005 826
70. P.G. Ciattini, E. Morera, and G. Ortar Synth. Commun. 25 1995 2883