Palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols

Tetrahedron

Volumn 67, Issue 33, 2011, Pages 5878-5882

  Luo, Fang ^a   Pan, Changduo ^b   Cheng, Jiang ^a   Chen, Fan ^a  

^a WENZHOU UNIVERSITY   (China)

^b Wenzhou Institute of Industry and Science   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; BENZYL ALCOHOL; FUNCTIONAL GROUP; OXYGEN; PALLADIUM; PHENOL DERIVATIVE;

ARTICLE; ESTERIFICATION; OXIDATION; PRIORITY JOURNAL;

EID: 79960210995     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.06.060     Document Type: Article

References (81)

1. R.C. Larock Comprehensive Organic Transformations 1989 VCH New York, NY p 966 and references therein
2. J. Otera Esterification: Methods, Reactions and Applications 2003 Wiley New York, NY
3. K. Ishihara, S. Ohara, and H. Yamamoto Science 290 2000 1140
4. A. Corma, L.T. Nemeth, M. Renz, and S. Valencia Nature 412 2001 423
5. H.E. Hoydonckx, D.E. De Vos, S. Chavan, and P.A. Jacobs Top. Catal. 27 2004 83
6. C.-T. Chen, and Y.S. Munot J. Org. Chem. 70 2005 8625
7. C.-G. Yang, and C. He J. Am. Chem. Soc. 127 2005 6966
8. G.W. Nyce, J.A. Lamboy, E.F. Connor, R. Waymouth, and M.J.L. Hedrick Org. Lett. 4 2002 3587
9. K. Ekoue-Kovi, and C. Wolf Chem. - Eur. J. 14 2008 6302
10. S.D. Sarkar, S. Grimme, and A. Studer J. Am. Chem. Soc. 132 2010 1190
11. K. Zeitler Angew. Chem., Int. Ed. 44 2005 7506
12. B.R. Travis, M. Sivakumar, G.O. Hollist, and B. Borhan Org. Lett. 5 2003 1031
13. S.-I. Kiyooka, Y. Wada, M. Ueno, T. Yokoyama, and R. Yokoyama Tetrahedron 63 2007 12695
14. L.M.N. Susan, W.C. Lai, K.F. Bastow, F.R. Chang, Y.C. Wu, and K.H. Lee Bioorg. Med. Chem. Lett. 20 2010 1037
15. R. Gopinath, and B.K. Patel Org. Lett. 2 2000 577
16. R. Gopinath, A.R. Paital, and B.K. Patel Tetrahedron Lett. 43 2002 5123
17. B. Barkakaty, B. Talukdar, and B.K. Patel J. Org. Chem. 68 2003 2944
18. W.-J. Yoo, and C.-J. Li J. Org. Chem. 71 2006 6266
19. G.-Q. Li, L.-X. Dai, and S.-L. You Org. Lett. 11 2009 1623
20. X.-F. Wu, and C. Darcel Eur. J. Org. Chem. 2009 1144
21. H. Jiang, B. Gschwend, Ł Albrecht, and K.A. Jørgensen Org. Lett. 12 2010 5052
22. S. Arita, T. Koike, Y. Kayaki, and T. Ikariya Chem. - Asian J. 3 2008 1479
23. T. Zweifel, J.-V. Naubron, T. Büttner, T. Ott, and H. Grützmacher Angew. Chem., Int. Ed. 47 2008 3245
24. N.A. Owston, A.J. Parker, and J.M.J. Williams Chem. Commun. 2008 624
25. T. Mitsudome, A. Noujima, T. Mizugaki, K. Jitsukawa, and K. Kaneda Green Chem. 11 2009 793
26. M.G. Coleman, A.N. Brown, B.A. Bolton, and H. Guana Adv. Synth. Catal. 352 2010 967
27. E.J. Corey, N.W. Gilman, and B.E. Ganem J. Am. Chem. Soc. 90 1968 5616
28. E.J. Corey, J.A. Katzenellenbogen, N.W. Gilman, S.A. Roman, and B.W. Erickson J. Am. Chem. Soc. 90 1968 5618
29. E.J. Corey, and B. Samuelsson J. Org. Chem. 49 1984 4735
30. N. Mori, and H. Togo Tetrahedron 61 2005 5915
31. S.-I. Murahashi, T. Naota, K. Ito, Y. Maeda, and H. Taki J. Org. Chem. 52 1987 4319
32. T. Suzuki, K. Morita, M. Tsuchida, and K. Hiroi Org. Lett. 4 2002 2361
33. J. Zhao, and J.F. Hartwig Organometallics 24 2005 2441
34. M. Ito, A. Osaku, A. Shiibashi, and T. Ikariya Org. Lett. 9 2007 1821
35. J. Zhang, G. Leitus, Y. Ben-David, and D. Milstein J. Am. Chem. Soc. 127 2005 10840
36. C. Gunanathan, L.J.W. Shimon, and D. Milstein J. Am. Chem. Soc. 131 2009 3146
37. B.E. Maki, A. Chan, E.M. Phillips, and K.A. Scheidt Org. Lett. 7 2007 371
38. B.E. Maki, A. Chan, E.M. Phillips, and K.A. Scheidt Tetrahedron 65 2009 3102
39. A. Moretto, A. Nicolli, and M. Lotti Toxicol. Appl. Pharmacol. 219 2007 196
40. M.D. Barratt, D.A. Basketter, and D.W. Roberts Toxicol. in Vitro 8 1994 823
41. C. James, and V. Snieckus J. Org. Chem. 74 2009 4080
42. U. Beginn, G. Zipp, and M. Moller Chem. - Eur. J. 6 2000 2016
43. F. Luo, C. Pan, P. Qian, and J. Cheng Synthesis 2010 2005
44. L. Zhang, G. Zhang, M. Zhang, and J. Cheng J. Org. Chem. 75 2010 7472
45. Z. Ye, W. Wang, F. Luo, S. Zhang, and J. Cheng Org. Lett. 11 2009 3974
46. W. Wang, C. Pan, F. Chen, and J. Cheng Chem. Commun. 47 2011 3978
47. J.-J. Dai, J.-H. Liu, D.-F. Luo, and L. Liu Chem. Commun. 47 2011 677
48. F. Luo, C. Pan, P. Qian, and J. Cheng J. Org. Chem. 75 2010 5379
49. C. Qin, H. Wu, J. Chen, M. Liu, J. Cheng, W. Su, and J. Ding Org. Lett. 10 2008 1537
50. J.N. Rosa, R.S. Reddy, N.R. Candeias, P.M.S.D. Cal, and P.M.P. Gois Org. Lett. 12 2010 2686
51. Z. Ye, G. Lv, W. Wang, M. Zhang, and J. Cheng Angew. Chem., Int. Ed. 49 2010 3671
52. Z. Ye, P. Qian, G. Lv, F. Luo, and J. Cheng J. Org. Chem. 75 2010 6043
53. F. Luo, S. Pan, C. Pan, P. Qian, and J. Cheng Adv. Synth. Catal. 353 2011 320
54. M. Zhang, S. Zhang, G. Zhang, F. Chen, and J. Cheng Tetrahedron Lett. 52 2011 2480
55. C. Liu, J. Wang, L. Meng, Y. Deng, Y. Li, and A. Lei Angew. Chem., Int. Ed. 50 2011 5144
56. S. Gowrisankar, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 50 2011 5139
57. A. Chan, and K.A. Scheidt Org. Lett. 7 2005 905
58. K. Zeitler, and C.A. Rose J. Org. Chem. 74 2009 1759
59. Esterification of alkynyl aldehydes to α, β-unsaturated carboxylic esters, please see: K. Zeitler Org. Lett. 8 2006 637
60. S.S. Stahl Angew. Chem., Int. Ed. 43 2004 3400
61. B.V. Popp, and S.S. Stahl J. Am. Chem. Soc. 129 2007 4410
62. B.A. Steinhoff, and S.S. Stahl Org. Lett. 4 2002 4179
63. M.S. Sigman, and D.R. Jensen Acc. Chem. Res. 39 2006 221
64. N. Kakiuchi, Y. Maeda, T. Nishimura, and S. Uemura J. Org. Chem. 66 2001 6620
65. T. Nishimura, T. Onoue, K. Ohe, and S. Uemura J. Org. Chem. 64 1999 6750
66. K.P. Peterson, and R.C. Larock J. Org. Chem. 63 1998 3185
67. G.-J. Brink, I.W.C.E. Arends, and R.A. Sheldon Adv. Synth. Catal. 344 2002 355
68. M.J. Schultz, C.C. Park, and M.S.A. Sigman Chem. Commun. 2002 3034
69. J. Chen, Q. Zhang, Y. Wang, and H. Wan Adv. Synth. Catal. 350 2008 453
70. A.K. Chakraborti, and Shivani J. Org. Chem. 71 2006 5785
71. M. Hosseini Sarvari, and H. Sharghi Tetrahedron 61 2005 10903
72. J. Deutsch, A. Trunschke, D. Muller, V. Quaschning, E. Kemnitz, and H. Lieske J. Mol. Catal. A: Chem. 207 2004 51
73. N. Iranpoor, H. Firouzabadi, D. Khalili, and S. Motevalli J. Org. Chem. 73 2008 4882
74. C. Marette, C. Larrouquet, P. Tisnes, J.-B. Deloye, and E. Gras Tetrahedron Lett. 47 2006 6947
75. V. Polshettiwar, and M.P. Kaushik Catal. Commun. 6 2005 191
76. J.-J. Li, and T.D.H. Bugg Org. Biomol. Chem. 5 2007 507
77. I.-H. Um, J.-Y. Lee, H. Lee, Y. Nagano, M. Fujio, and Y. Tsuno J. Org. Chem. 70 2005 4980
78. C. Hubbard, and J. Kirsch Biochemistry 11 1972 2483
79. T. Kurz, M.K. Pein, L. Marek, C.T. Behrendt, L. Spanier, K. Kuna, and K. Bruecher Eur. J. Org. Chem. 2009 2939
80. D.A. Watson, X. Fan, and S.L. Buchwald J. Org. Chem. 73 2008 7096
81. F. Ishikawa, T. Tsumuraya, and I. Fujii J. Am. Chem. Soc. 131 2009 456