Highly selective acetoxylation of sulfonamides via using phenyliodine(III) diacetate

Tetrahedron

Volumn 70, Issue 38, 2014, Pages 6879-6884

  Wang, Sichang ^a   Ni, Zhangqin ^a   Wang, Yanjie ^b   Pang, Yihui ^a   Pan, Yuanjiang ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

para Acetoxylation ortho Acetoxylation N Phenylbenzenesulfonamides

Indexed keywords

ACETOACETIC ACID DERIVATIVE; PHENYLIODINE DIACETATE; SULFONAMIDE; UNCLASSIFIED DRUG;

ACETOXYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; OXIDATION; STOICHIOMETRY; SYNTHESIS;

EID: 84906962386     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.07.007     Document Type: Article

References (65)

1. P.M. Henry Catalysis by Metal Complexes Palladium Catalyzed Oxidation of Hydrocarbons Vol. 2 1980 Reidel Dordrecht, The Netherlands
2. A.E. Shilov, and G.B. Shul'pin Chem. Rev. 97 1997 2879 2932
3. A. Sen Acc. Chem. Res. 31 1998 550 557
4. S.S. Stahl, J.A. Labinger, and J.E. Bercaw Angew. Chem., Int. Ed. 37 1998 2181 2192
5. J.T. Groves J. Porphyrins Phthalocyanines 4 2000 350 352
6. U. Fekl, and K.I. Goldberg Adv. Inorg. Chem. 54 2003 259 320
7. J. Tsuji Palladium in Organic Synthesis 2005 Springer Berlin, Germany
8. J. Tsuji Palladium Reagents and Catalysts: New PerspectiVes for the 21st Century 2nd ed. 2004 Wiley West Sussex, UK
9. A. de Meijere, and F. Diederich Metal-catalyzed Cross-coupling Reactions 2nd ed. 2004 Wiley-VCH Weinheim, Germany
10. E.I. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis Vols. 1 and 2 2002 John Wiley and Sons New York, NY
11. For recent reviews, see: A.R. Dick, and M.S. Sanford Tetrahedron 62 2006 2439 2463
12. O. Daugulis, V.G. Zaitsev, D. Shabashov, Q.N. Pham, and A. Lazareva Synlett 2006 3382 3388
13. J.-Q. Yu, R. Giri, and X. Chen Org. Biomol. Chem. 4 2006 4041 4047
14. N.R. Deprez, and M.S. Sanford Inorg. Chem. 46 2007 1924 1935
15. H.Y. Thu, W.Y. Yu, and C.M. Che J. Am. Chem. Soc. 128 2006 9048 9049
16. X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, and Z. Shi J. Am. Chem. Soc. 128 2006 7416 7417
17. A.R. Dick, K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 126 2004 2300 2301
18. L.V. Desai, K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 126 2004 9542 9543
19. W.C.P. Tsang, N. Zheng, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 14560 14561
20. A.R. Dick, J.W. Kampf, and M.S. Sanford J. Am. Chem. Soc. 127 2005 12790 12791
21. R.S. Xu, J.P. Wan, H. Mao, and Y.J. Pan J. Am. Chem. Soc. 132 2010 15531 15532
22. T. Yoneyama, and R.H. Crabtree J. Mol. Catal. A: Chem. 108 1996 35 40
23. K. Muz Angew. Chem., Int. Ed. 48 2009 9412 9423
24. L.M. Xu, B.J. Li, Z. Yang, and Z.J. Shi Chem. Soc. Rev. 39 2010 712 733
25. J.M. Racowski, A.R. Dick, and M.S. Sanford J. Am. Chem. Soc. 131 2009 10974 10983
26. S.R. Neufeldt, and M.S. Sanford Org. Lett. 12 2010 532 535
27. T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147 1169
28. R. Moriarty, M.O. Prakash, and P.R. Vavilikolanu Synth. Commun. 16 1986 1247 1253
29. L.R. Subramanian Sci. Synth. 19 2004 79 173
30. S.H.H. Kim, S. Lee, S.H. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 5863 5866
31. Y.H. Zhang, and J.Q. Yu J. Am. Chem. Soc. 131 2009 14654 14655
32. T.S. Mei, R. Giri, N. Maugel, and J.Q. Yu Angew. Chem., Int. Ed. 47 2008 5215 5219
33. A.J. Canty, M.C. Denney, G. Koten, B.W. Skelton, and A.H. White Organometallics 23 2004 5432 5439
34. Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, and S. Oka J. Am. Chem. Soc. 116 1994 3684 3691
35. Y. Kikugawa, and N. Itoh J. Org. Chem. 67 2002 7424 7428
36. Y.-M. Liang, and F.R. Gou Org. Lett. 11 2009 5726 5729
37. A. Pialat, B. Liégault, and M. Taillefer Org. Lett. 15 2013 1764 1767
38. J.Q. Yu, and R. Giri Angew. Chem., Int. Ed. 44 2005 7420 7424
39. O.-G. Mancheño, and H. Richter Adv. Synth. Catal. 353 2011 295 302
40. G.-W. Wang, and T.-T. Yuan J. Org. Chem. 73 2008 4717 4720
41. Y.-H. Gu, and H. Liu Org. Biomol. Chem. 9 2011 1614 1620
42. Y.-H. Gu, and H. Liu Tetrahedron Lett. 52 2011 4324 4326
43. R. Samanta, R. Lategahn, and A.P. Antonchick Chem. Commun. 2012 3194 3196
44. M. Uyanik, and K. Ishihara Chem. Commun. 2009 2086 2099
45. T. Dohi, and Y. Kita Chem. Commun. 2009 2073 2085
46. V.V. Zhdankin, and P.J. Stang Chem. Rev. 108 2008 5299 5358
47. R. Samanta, K. Matcha, and A.P. Antonchick Eur. J. Org. Chem. 78 2013 5769 5804
48. M. Ochiai, and K. Miyamoto Eur. J. Org. Chem. 73 2008 4229 4239
49. V.V. Zhdankin Sci. Synth. 31a 2007 161 234
50. T. Wirth Angew. Chem., Int. Ed. 44 2005 3656 3665
51. R.M. Moriarty J. Org. Chem. 70 2005 2893 2903
52. H. Tohma, and Y. Kita Adv. Synth. Catal. 346 2004 111 124
53. T. Wirth HyperValent Iodine Chemistry 2003 Springer Berlin, Heidelberg
54. V.V. Zhdankin, and P.J. Stang Chem. Rev. 102 2002 2523 2584
55. P.J. Stang, and V.V. Zhdankin Chem. Rev. 96 1996 1123 1178
56. Y. Kita, T. Takada, and H. Tohma Pure Appl. Chem. 68 1996 627 630
57. A. Varvoglis HyperValent Iodine in Organic Synthesis 1997 Academic San Diego, CA
58. T. Kitamura, and Y. Fujiwara Org. Prep. Proced. Int. 29 1997 409 458
59. M. Ochiai K. Akiba, Chemistry in HyperValent Compounds 1999 Wiley-VCH New York, NY Chapter 12
60. Y. Kita, and T. Dohi J. Org. Chem. 72 2007 109 116
61. M. Banerjee, A. Poddar, and G. Mitra J. Med. Chem. 48 2005 547 555
62. A. Natarajan, Y. Guo, F. Harbinski, and Y.H.H. Fan J. Med. Chem. 47 2004 4979 4982
63. H. Yoshino, N. Ueda, and J. Niijima J. Med. Chem. 35 1992 2496 2497
64. H.F. Jiang, X.D. Tang, and L.B. Huang Chem. Commun. 2013 6102 6104
65. T. Tian, W.H. Zhong, X.B. Meng, and Z.J. Li J. Org. Chem. 78 2013 728 732