Gold-catalyzed intermolecular C-S bond formation: Efficient synthesis of α-substituted vinyl sulfones

Angewandte Chemie - International Edition

Volumn 53, Issue 18, 2014, Pages 4657-4661

  Xi, Yumeng ^a   Dong, Boliang ^a   McClain, Edward J ^a   Wang, Qiaoyi ^a   Gregg, Tesia L ^a   Akhmedov, Novruz G ^a   Petersen, Jeffrey L ^a   Shi, Xiaodong ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

C S bond formation; gold; Lewis acids; Markovnikov addition; vinyl sulfones

Indexed keywords

CATALYSIS; CHEMICAL BONDS; GOLD; HYDROCARBONS;

1 ,2-DICHLOROETHANES; C-S BOND FORMATIONS; EFFICIENT SYNTHESIS; GALLIUM TRIFLATE; LEWIS ACID; MARKOVNIKOV ADDITION; ONE-POT SYNTHESIS; VINYL SULFONES;

GOLD COMPOUNDS;

EID: 84899511760     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201310142     Document Type: Article

References (102)

1. A. Vigalok, C-X Bond Formation, Springer, Heidelberg, 2010
2. A. K. Yudin, Catalyzed Carbon-Heteroatom Bond Formation, Wiley-VCH, Weinheim, 2012
3. H. Liu, X. Jiang, Chem. Asian J. 2013, 8, 2546.
4. J. T. Palmer, D. Rasnick, J. L. Klaus, D. Bromme, J. Med. Chem. 1995, 38, 3193
5. M. M. M. Santos, R. Moreira, Mini-Rev. Med. Chem. 2007, 7, 1040
6. I. D. Kerr, J. H. Lee, C. J. Farady, R. Marion, M. Rickert, M. S. Kailash, C. Pandey, C. R. Caffrey, J. Legac, E. Hansell, J. H. McKerrow, C. S. Craik, P. J. Rosenthal, L. S. Brinen, J. Biol. Chem. 2009, 284, 25697
7. A. F. Kisselev, W. A. van der Linden, H. S. Overkleeft, Chem. Biol. 2012, 19, 99
8. L. Ni, X. S. Zheng, P. K. Somers, L. K. Hoong, R. R. Hill, E. M. Marino, K.-L. Suen, U. Saxena, C. Q. Meng, Bioorg. Med. Chem. Lett. 2003, 13, 745.
9. J. Morales-Sanfrutos, J. Lopez-Jaramillo, M. Ortega-Munoz, A. Megia-Fernandez, F. Perez-Balderas, F. Hernandez-Mateo, F. Santoyo-Gonzalez, Org. Biomol. Chem. 2010, 8, 667
10. F. J. Lopez-Jaramillo, F. Hernandez-Mateo, F. Santoyo-Gonzalez, Integrative Proteomics (Ed.:, H.-C. E. Leung,), InTech, Rijeka, 2012, pp. 301-327.
11. V. Nair, A. Augustine, T. D. Suja, Synthesis 2002, 2259
12. D. C. Meadows, J. Gervay-Hague, Med. Res. Rev. 2006, 26, 793
13. H. Qian, X. Huang, Synlett 2001, 1913
14. X. Huang, D. Duan, W. Zheng, J. Org. Chem. 2003, 68, 1958
15. W. M. Xu, E. Tang, X. Huang, Synthesis 2004, 2094
16. D. Díez, P. García, I. S. Marcos, N. M. Garrido, P. Basabe, H. B. Broughton, J. G. Urones, Tetrahedron 2005, 61, 699
17. Z.-H. Guan, W. Zuo, L.-B. Zhao, Z.-H. Ren, Y.-M. Liang, Synthesis 2007, 1465
18. G. Signore, C. Malanga, R. Menicagli, Tetrahedron 2008, 64, 11218
19. B. Das, M. Lingaiah, K. Damodar, N. Bhunia, Synthesis 2011, 2941
20. S. Liang, R.-Y. Zhang, G. Wang, S.-Y. Chen, X.-Q. Yu, Eur. J. Org. Chem. 2013, 7050.
21. J. M. Baskin, Z. Wang, Org. Lett. 2002, 4, 4423
22. V. Nair, A. Augustine, T. G. George, L. G. Nair, Tetrahedron Lett. 2001, 42, 6763
23. S. Cacchi, G. Fabrizi, A. Goggiamani, L. M. Parisi, R. Bernini, J. Org. Chem. 2004, 69, 5608
24. A. Battace, T. Zair, H. Doucet, M. Santelli, Synthesis 2006, 3495
25. F. Huang, R. A. Batey, Tetrahedron 2007, 63, 7667
26. M. Bian, F. Xu, C. Ma, Synthesis 2007, 2951
27. D. C. Reeves, S. Rodriguez, H. Lee, N. Haddad, D. Krishnamurthy, C. H. Senanayake, Tetrahedron Lett. 2009, 50, 2870
28. Q.-L. Xu, L.-X. Dai, S.-L. You, Org. Lett. 2010, 12, 800
29. N. Taniguchi, Synlett 2011, 1308
30. N. Taniguchi, Synlett 2012, 1245.
31. Radical intermediates favor anti-Markovnikov addition; see Ref. [5i] and:, Q. Lu, J. Zhang, G. Zhao, Y. Qi, H. Wang, A. Lei, J. Am. Chem. Soc. 2013, 135, 11481.
32. R. Chawla, R. Kapoor, A. K. Singh, L. D. S. Yadav, Green Chem. 2012, 14, 1308
33. J. W. Lee, C.-W. Lee, J. H. Jung, D. Y. Oh, Synth. Commun. 2000, 30, 2897
34. K. Inomata, S.-i. Sasaoka, T. Kobayashi, Y. Tanaka, S. Igarashi, T. Ohtani, H. Kinoshita, H. Kotake, Bull. Chem. Soc. Jpn. 1987, 60, 1767
35. K. Inomata, T. Kobayashi, S.-i. Sasaoka, H. Kinoshita, H. Kotake, Chem. Lett. 1986, 15, 289
36. J. B. Hendrickson, P. S. Palumbo, Tetrahedron Lett. 1985, 26, 2849
37. C.-N. Hsiao, H. Shechter, Tetrahedron Lett. 1982, 23, 3455
38. T. G. Back, S. Collins, J. Org. Chem. 1981, 46, 3249
39. H. Kotake, K. Inomata, M. Sumita, Chem. Lett. 1978, 7, 717
40. S. Chodroff, W. Whitmore, J. Am. Chem. Soc. 1950, 72, 1073.
41. A. S. K. Hashmi, F. D. Toste, Modern Gold Catalyzed Synthesis, Wiley-VCH, Weinheim, 2012
42. A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2012, 41, 2448
43. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351
44. A. Arcadi, Chem. Rev. 2008, 108, 3266
45. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326
46. R. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382
47. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180
48. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478
49. Angew. Chem. Int. Ed. 2007, 46, 3410
50. L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271
51. A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064
52. Angew. Chem. Int. Ed. 2006, 45, 7896.
53. N. Morita, N. Krause, Angew. Chem. 2006, 118, 1930
54. Angew. Chem. Int. Ed. 2006, 45, 1897
55. I. Nakamura, T. Sato, Y. Yamamoto, Angew. Chem. 2006, 118, 4585-4587
56. Angew. Chem. Int. Ed. 2006, 45, 4473-4475
57. P. W. Davies, S. J. C. Albrecht, Chem. Commun. 2008, 238
58. I. Nakamura, T. Sato, M. Terada, Y. Yamamoto, Org. Lett. 2008, 10, 2649
59. L. L. Santos, V. R. Ruiz, M. J. Sabater, A. Corma, Tetrahedron 2008, 64, 7902
60. A. Aponick, C.-Y. Li, J. Malinge, E. F. Marques, Org. Lett. 2009, 11, 4624
61. X. Zhao, Z. Zhong, L. Peng, W. Zhang, J. Wang, Chem. Commun. 2009, 2535
62. P. W. Davies, S. J. C. Albrecht, Angew. Chem. 2009, 121, 8522
63. Angew. Chem. Int. Ed. 2009, 48, 8372
64. M. Jean, J. Renault, P. van de Weghe, N. Asao, Tetrahedron Lett. 2010, 51, 378
65. R. J. Mudd, P. C. Young, J. A. Jordan-Hore, G. M. Rosair, A.-L. Lee, J. Org. Chem. 2012, 77, 7633
66. A. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657.
67. P. C. Young, S. L. J. Green, G. M. Rosair, A.-L. Lee, Dalton Trans. 2013, 42, 9645.
68. N. D. Shapiro, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 4160
69. G. Li, L. Zhang, Angew. Chem. 2007, 119, 5248
70. Angew. Chem. Int. Ed. 2007, 46, 5156
71. C.-W. Li, K. Pati, G.-Y. Lin, H.-H. Hung, R.-S. Liu, Angew. Chem. 2010, 122, 10087
72. Angew. Chem. Int. Ed. 2010, 49, 9891
73. B. Lu, Y. Li, Y. Wang, D. H. Aue, Y. Luo, L. Zhang, J. Am. Chem. Soc. 2013, 135, 8512.
74. D. De Filippo, F. Momicchioli, Tetrahedron 1969, 25, 5733.
75. B. C. Chary, S. Kim, J. Org. Chem. 2010, 75, 7928
76. T. Luo, M. Dai, S. L. Zheng, S. L. Schreiber, Org. Lett. 2011, 13, 2834
77. M. R. Kuram, M. Bhanuchandra, A. K. Sahoo, J. Org. Chem. 2010, 75, 2247
78. P. H. Lee, S. Kim, A. Park, B. C. Chary, S. Kim, Angew. Chem. 2010, 122, 6958
79. Angew. Chem. Int. Ed. 2010, 49, 6806. Sulfonic acids are also suitable substrates for such addition reactions; see
80. D.-M. Cui, Q. Meng, J.-Z. Zheng, C. Zhang, Chem. Commun. 2009, 1577.
81. L. Ye, W. He, L. Zhang, Angew. Chem. 2011, 123, 3294
82. Angew. Chem. Int. Ed. 2011, 50, 3236.
83. H. Duan, S. Sengupta, J. L. Petersen, N. G. Akhmedov, X. Shi, J. Am. Chem. Soc. 2009, 131, 12100
84. Y. Chen, W. Yan, N. G. Akhmedov, X. Shi, Org. Lett. 2010, 12, 344
85. D. Wang, X. Ye, X. Shi, Org. Lett. 2010, 12, 2088
86. D. Wang, L. N. S. Gautam, C. Bollinger, A. Harris, M. Li, X. Shi, Org. Lett. 2011, 13, 2618
87. Q. Wang, S. Aparaj, N. G. Akhmedov, J. L. Petersen, X. Shi, Org. Lett. 2012, 14, 1334
88. D. Wang, R. Cai, S. Sharma, J. Jirak, S. K. Thummanapelli, N. G. Akhmedov, H. Zhang, X. Liu, J. L. Petersen, X. Shi, J. Am. Chem. Soc. 2012, 134, 9012
89. Y. Xi, B. Dong, X. Shi, Beilstein J. Org. Chem. 2013, 9, 2537
90. Y. Yu, W. Yang, F. Rominger, A. S. K. Hashmi, Angew. Chem. 2013, 125, 7735
91. Angew. Chem. Int. Ed. 2013, 52, 7586
92. Y. Xi, D. Wang, X. Ye, N. G. Akhmedov, J. L. Petersen, X. Shi, Org. Lett. 2014, 16, 306
93. Y. Xi, Q. Wang, Y. Su, M. Li, X. Shi, Chem. Commun. 2014, 50, 2158
94. Q. Wang, S. E. Motika, N. G. Akhmedov, J. L. Petersen, X. Shi, Angew. Chem. 2014, DOI
95. Angew. Chem. Int. Ed. 2014, DOI:.
96. CCDC 966046 (3 bh) 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.
97. J.-E. Bäckvall, R. Chinchilla, C. Najera, M. Yus, Chem. Rev. 1998, 98, 2291
98. T. G. Back, K. N. Clary, D. Gao, Chem. Rev. 2010, 110, 4498.
99. J.-E. Baeckvall, S. K. Juntunen, J. Am. Chem. Soc. 1987, 109, 6396
100. T.-S. Chou, S.-C. Hung, J. Org. Chem. 1988, 53, 3020
101. R. F. de la Pradilla, C. Montero, M. Tortosa, A. Viso, Chem. Eur. J. 2005, 11, 5136.
102. T. G. Back, M. Parvez, H. Zhai, J. Org. Chem. 2003, 68, 9389.