Iodine-catalyzed intramolecular oxidative thiolation of vinylic carbon-hydrogen bonds via tandem iodocyclization and dehydroiodination: Construction of 2-methylene-3-thiophenones

Advanced Synthesis and Catalysis

Volumn 356, Issue 4, 2014, Pages 743-748

  Zheng, Gang ^a   Ma, Xiaoli ^a   Liu, Bangyu ^a   Dong, Ying ^a   Wang, Mang ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

carbon sulfur bond formation; heterocycles; iodine; selectivity; synthetic methods

Indexed keywords

EID: 84896401349     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300815     Document Type: Article

References (93)

1. T. Kondo, T.-A. Mitsudo, Chem. Rev. 2000, 100, 3205
2. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558
3. Angew. Chem. Int. Ed. 2003, 42, 5400
4. I. P. Beletskaya, V. P. Ananikov, Eur. J. Org. Chem. 2007, 3431
5. I. P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596
6. C. C. Eichman, J. P. Stambuli, Molecules 2011, 16, 590
7. H. Liu, X. Jiang, Chem. Asian J. 2013, 8, 2546.
8. F. J. Robertson, J. Wu, J. Am. Chem. Soc. 2012, 134, 2775
9. D. H. Scharf, N. Remme, A. Habel, P. Chankhamjon, K. Scherlach, T. Heinekamp, P. Hortschansky, A. A. Brakhage, C. Hertweck, J. Am. Chem. Soc. 2011, 133, 12322
10. B. Jiang, H. Tian, A.-G. Huang, M. Xu, Org. Lett. 2008, 10, 2737
11. K. Oh, Org. Lett. 2007, 9, 2973
12. C. S. Bryan, J. A. Braunger, M. Lautens, Angew. Chem. 2009, 121, 7198
13. Angew. Chem. Int. Ed. 2009, 48, 7064
14. B. Gabriele, R. Mancuso, G. Salerno, R. C. Larock, J. Org. Chem. 2012, 77, 7640
15. Q. Zhao, L. Li, Y. Fang, D. Sun, C. J. Li, J. Org. Chem. 2009, 74, 459
16. H. Mizuno, K. Domon, K. Masuya, K. Tanino, I. Kuwajima, J. Org. Chem. 1999, 64, 2648.
17. Y.-Y. Lin, Y.-J. Wang, C.-H. Lin, J.-H. Cheng, C.-F. Lee, J. Org. Chem. 2012, 77, 6100
18. Q. Liao, C. Xi, Chin. J. Org. Chem. 2012, 32, 986
19. H.-L. Kao, C.-F. Lee, Org. Lett. 2011, 13, 5204
20. W. You, X. Yan, Q. Liao, C. Xi, Org. Lett. 2010, 12, 3930
21. M. S. Kabir, M. Lorenz, M. L. Van Linn, O. A. Namjoshi, S. Ara, J. M. Cook, J. Org. Chem. 2010, 75, 3626
22. M. S. Kabir, M. L. Van Linn, A. Monte, J. M. Cook, Org. Lett. 2008, 10, 3363
23. C.-K. Chen, Y.-W. Chen, C.-H. Lin, H.-P. Lin, C.-F. Lee, Chem. Commun. 2010, 46, 282
24. V. P. Reddy, A. V. Kumar, K. Swapna, K. R. Rao, Org. Lett. 2009, 11, 1697
25. E. Sperotto, G. P. M. van Klink, J. G. de Vries, G. van Koten, J. Org. Chem. 2008, 73, 5625
26. A. Correa, M. Carril, C. Bolm, Angew. Chem. 2008, 120, 2922
27. Angew. Chem. Int. Ed. 2008, 47, 2880
28. Y. Zhang, K. C. Ngeow, J. Y. Ying, Org. Lett. 2007, 9, 3495.
29. K. Liu, F. Jia, H. Xi, Y. Li, X. Zheng, Q. Guo, B. Shen, Z. Li, Org. Lett. 2013, 15, 2026
30. A. D. Giuseppe, R. Castarlenas, J. J. Pérez-Torrente, M. Crucianelli, V. Polo, R. Sancho, F. J. Lahoz, L. A. Oro, J. Am. Chem. Soc. 2012, 134, 8171
31. S. Ranjit, Z. Duan, P. Zhang, X. Liu, Org. Lett. 2010, 12, 4134
32. Z. Duan, S. Ranjit, P. Zhang, X. Liu, Org. Lett. 2010, 12, 2430
33. C. J. Weiss, T. J. Marks, J. Am. Chem. Soc. 2010, 132, 10533
34. Q. Ding, X. He, J. Wu, J. Comb. Chem. 2009, 11, 587.
35. C. I. Herrerías, X. Yao, Z. Li, C.-J. Li, Chem. Rev. 2007, 107, 2546
36. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
37. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
38. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879
39. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936
40. M. S. Sigman, E. W. Werner, Acc. Chem. Res. 2012, 45, 874
41. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
42. B. G. Hashiguchi, S. M. Bischof, M. M. Konnick, R. A. Periana, Acc. Chem. Res. 2012, 45, 885.
43. C. Yu, C. Zhang, X. Shi, Eur. J. Org. Chem. 2012, 1953
44. S. Ranjit, R. Lee, D. Heryadi, C. Shen, J. Wu, P. Zhang, K. Huang, X. Liu, J. Org. Chem. 2011, 76, 8999
45. A. Zhou, X. Liu, K. Yang, S. Zhao, Y. Liang, Org. Biomol. Chem. 2011, 9, 5456
46. S. Zhang, P. Qian, M. Zhang, M. Hu, J. Cheng, J. Org. Chem. 2010, 75, 6732.
47. C. Shen, H. Xia, H. Yan, X. Chen, S. Ranjit, X. Xie, D. Tan, R. Lee, Y. Yang, B. Xing, K. Huang, P. Zhang, X. Liu, Chem. Sci. 2012, 3, 2388
48. K. Inamoto, K. Nozawa, Y. Kondo, Synlett 2012, 10, 1678
49. J. Zhu, Z. Chen, H. Xie, S. Li, Y. Wu, Org. Lett. 2010, 12, 2434
50. K. Inamoto, C. Hasegawa, J. Kawasaki, K. Hiroya, T. Doi, Adv. Synth. Catal. 2010, 352, 2643
51. K. Inamoto, C. Hasegawa, J. Kawasaki, K. Hiroya, T. Doi, Org. Lett. 2008, 10, 5147
52. K. Inamoto, Y. Arai, K. Hiroya, T. Doi, Chem. Commun. 2008, 5529.
53. H. Wang, L. Wang, J. Shang, X. Li, H. Wang, J. Gui, A. Lei, Chem. Commun. 2012, 48, 76
54. M. L. Zhang, S. H. Zhang, C. D. Pan, F. Chen, Synth. Commun. 2012, 42, 2844
55. X. L. Fang, R. Y. Tang, X. G. Zhang, J. H. Li, Synthesis 2011, 1099.
56. L. Zou, J. Reball, J. Mottweiler, C. Bolm, Chem. Commun. 2012, 48, 11307.
57. M. T. Bresser, P. Knochel, Angew. Chem. 2011, 123, 1954
58. Angew. Chem. Int. Ed. 2011, 50, 1914
59. P. J. E. Verdegem, M. C. F. Monnee, J. Lugtenburg, J. Org. Chem. 2001, 66, 1269
60. L. Brandsma, H. D. Verkruijsse, C. Schade, P. von R. Schleyer, J. Chem. Soc. Chem. Commun. 1986, 260
61. J.-C. Clinet, C. Linstrumelle, Synthesis 1981, 875.
62. Y. Masaki, K. Sakuma, K. Kaji, Chem. Lett. 1979, 1235.
63. H. Takahata, K. Moriyama, M. Maruyama, T. Yamazaki, J. Chem. Soc. Chem. Commun. 1986, 1671
64. N. F. Haley, M. W. Fichtner, J. Org. Chem. 1980, 45, 2959.
65. L. Pan, X. Bi, Q. Liu, Chem. Soc. Rev. 2013, 42, 1251
66. L. Pan, Q. Liu, Synlett 2011, 1073.
67. B. Liu, G. Zheng, X. Liu, C. Xu, J. Liu, M. Wang, Chem. Commun. 2013, 49, 2201
68. M. Wang, F. Han, H. Yuan, Q. Liu, Chem. Commun. 2010, 46, 2247
69. M. Wang, Z. Fu, F. Han, Y. Dong, J. Liu, Q. Liu, Chem. Commun. 2010, 46, 9061
70. Z. Fu, M. Wang, Y. Dong, J. Liu, Q. Liu, J. Org. Chem. 2009, 74, 6105
71. Y. Ma, M. Wang, D. Li, B. Bekturhun, J. Liu, Q. Liu, J. Org. Chem. 2009, 74, 3116.
72. M. J. Mphahlele, Molecules 2009, 14, 4814
73. B. Godoi, R. F. Schumacher, G. Zeni, Chem. Rev. 2011, 111, 2937
74. P. T. Parvatkar, P. S. Parameswaran, S. G. Tilve, Chem. Eur. J. 2012, 18, 5460.
75. 2=0.0825 [I>2 s(I)]. CCDC 947706 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
76. F.-L. Yang, S.-K. Tian, Angew. Chem. 2013, 125, 5029
77. Angew. Chem. Int. Ed. 2013, 52, 4929
78. J. Dhineshkumar, M. Lamani, K. Alagiri, K. R. Prabhu, Org. Lett. 2013, 15, 1092
79. Y. C. Teo, S. N. Riduan, Y. Zhang, Green Chem. 2013, 15, 2365
80. Y. Yan, Y. Zhang, C. Feng, Z. Zha, Z. Wang, Angew. Chem. 2012, 124, 8201
81. Angew. Chem. Int. Ed. 2012, 51, 8077
82. H. Batchu, S. Bhattacharyya, S. Batra, Org. Lett. 2012, 14, 6330
83. Y.-P. Zhu, M. Lian, F.-C. Jia, M.-C. Liu, J.-J. Yuan, Q.-H. Gao, A.-X. Wu, Chem. Commun. 2012, 48, 9086
84. Y. Zhu, M. Liu, F. Jia, J. Yuan, Q. Gao, M. Lian, A. Wu, Org. Lett. 2012, 14, 3392
85. Z. He, W. Liu, Z. Li, Chem. Asian J. 2011, 6, 1340.
86. M. Gao, Y. Yang, Y. D. Wu, C. Deng, W. M. Shu, D. X. Zhang, L. P. Cao, N. F. She, A. X. Wu, Org. Lett. 2010, 12, 4026
87. G. Yin, B. Zhou, X. Meng, A. Wu, Y. Pan, Org. Lett. 2006, 8, 2245
88. W. Ge, Y. Wei, Green Chem. 2012, 14, 2066.
89. T. Aida, N. Furukawa, S. Oae, Tetrahedron Lett. 1973, 14, 3853
90. T. Aida, T. Akasaka, N. Furukawa, S. Oae, Bull. Chem. Soc. Jpn. 1976, 49, 1117.
91. J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734.
92. Y. Dong, M. Wang, J. Liu, W. Ma, Q. Liu, Chem. Commun. 2011, 47, 2080
93. Y. Liu, M. Wang, H. Yuan, Q. Liu, Adv. Synth. Catal. 2010, 352, 884.