Sulfur(IV)-mediated transformations: From ylide transfer to metal-free arylation of carbonyl compounds

Journal of the American Chemical Society

Volumn 135, Issue 19, 2013, Pages 7312-7323

  Huang, Xueliang ^a   Patil, Mahendra ^a   Farès, Christophe ^a   Thiel, Walter ^a   Maulide, Nuno ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; CARBONYL DERIVATIVES; MECHANISTIC STUDIES; REACTION PATHWAYS;

AROMATIC COMPOUNDS; DENSITY FUNCTIONAL THEORY;

REACTION KINETICS;

ORGANIC COMPOUND; SULFUR; UNCLASSIFIED DRUG; YLIDE;

ARTICLE; ARYLATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

HYDROCARBONS, AROMATIC; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; QUANTUM THEORY; SULFOXIDES; SULFUR;

EID: 84877835173     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4017683     Document Type: Article

References (115)

1. Shen, T. Y. Angew. Chem., Int. Ed. Engl. 1972, 11, 460
2. Johansson, C. C. C.; Colacot, T. J. Angew Chem. Int. Ed. 2010, 49, 676
3. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082
4. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450
5. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234
6. For a recent account on metal-free arylation, see: Dichiarante, V.; Fagnoni, M. Synlett 2008, 787
7. Barton, D. H. R.; Finet, J.-P. Pure Appl. Chem. 1987, 59, 937
8. Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039
9. Finet, J.-P. Chem. Rev. 1989, 89, 1487
10. Elliott, G.; Konopelski, J. P. Tetrahedron 2001, 57, 5683
11. Ooi, T.; Goto, R.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 10494
12. Matano, Y.; Imahori, H. J. Org. Chem. 2004, 69, 5505
13. Koech, P. K.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 5350
14. Orito, K.; Sasaki, T.; Suginome, H. J. Org. Chem. 1995, 60, 6208
15. Morgan, J.; Pinhey, J. T.; Rowe, B. R. J. Chem. Soc., Perkin Trans. 1 1997, 1005
16. Elliott, G. I.; Konopelski, J. P.; Olmstead, M. M. Org. Lett. 1999, 1, 1867
17. Deng, H.; Konopelski, J. P. Org. Lett. 2001, 3, 3001
18. Xia, J.; Brown, L. E.; Konopelski, J. P. J. Org. Chem. 2007, 72, 6885
19. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
20. Olofsson, B.; Merritt, E. A. Angew. Chem., Int. Ed. 2009, 48, 9052
21. Aggarwal, V. K.; Olofsson, B. Angew. Chem., Int. Ed. 2005, 44, 5516
22. Eastman, K.; Baran, P. S. Tetrahedron 2009, 65, 3149
23. Norrby, P.-O.; Petersen, T. B.; Bielawski, M.; Olofsson, B. Chem.-Eur. J. 2010, 16, 8251
24. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260
25. Bigot, A.; Williamson, A. E.; Gaunt, M. J. J. Am. Chem. Soc. 2011, 133, 13778
26. Harvey, J. S.; Simonovich, S. P.; Jamison, C. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 13782
27. Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340
28. Ramtohul, Y.; Chartrand, A. Org. Lett. 2007, 9, 1029
29. Liu, Y. -L.; Liang, Y.; Pi, S. -F.; Li, J.-H. J. Org. Chem. 2009, 74, 5691
30. Tadross, P. M.; Gilmore, C. D.; Bugga, P.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1224
31. Bella, M.; Kobbelgaard, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 3670
32. Kobbelgaard, S.; Bella, M.; Jørgensen, K. A. J. Org. Chem. 2006, 71, 4980
33. Prüger, B.; Holmeister, G. E.; Jacobsen, C. B.; Alberg, D. G.; Nielsen, M.; Jørgensen, K. A. Chem.-Eur. J. 2010, 16, 3783
34. Bogle, K. M.; Hirst, D. J.; Dixon, D. J. Org. Lett. 2007, 9, 4901
35. Alemán, J.; Richter, B.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5515
36. Alemán, J.; Cabrera, S.; Maerten, E.; Overgaard, J.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5520
37. Jensen, K. L.; Franke, P. T.; Nielsen, L. T.; Daasbjerg, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2010, 49, 129
38. Conrad, J. C.; Kong, J.; Laforteza, B. N.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 11640
39. Nicolaou, K. C.; Reingruber, R.; Sarlah, D.; Bräse, S. J. Am. Chem. Soc. 2009, 131, 2086
40. Um, J. M.; Gutierrez, O.; Schoenebeck, F.; Houk, K. N.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 6001
41. Mart, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 2339
42. Mart, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 2341
43. Mart, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 4327
44. Arhart, R. J.; Mart, J. C. J. Am. Chem. Soc. 1972, 94, 5003
45. Mart, J. C.; Franz, J. A.; Arhart, R. J. J. Am. Chem. Soc. 1974, 96, 4604
46. Huang, X.; Goddard, R.; Maulide, N. Angew. Chem., Int. Ed. 2010, 49, 8979
47. Huang, X.; Peng, B.; Luparia, M.; Gomes, L. F. R.; Veiros, L. F.; Maulide, N. Angew. Chem., Int. Ed. 2012, 51, 8886
48. Huang, X.; Klimczyk, S.; Veiros, L. F.; Maulide, N. Chem. Sci. 2013, 4, 1105
49. Huang, X.; Goddard, R.; Maulide, N. Chem. Commun. 2013, 49, 4292
50. Huang, X.; Maulide, N. J. Am. Chem. Soc. 2011, 133, 8510
51. Trost, B. M.; Melvin, L. S. Sulfur Ylide, Academic Press, New York, 1975.
52. Li, A. -H.; Dai, L. -X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341
53. Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611
54. Tang, Y.; Ye, S.; Sun, X. -L. Synlett 2005, 2720
55. McGarrigle, E. M.; Meyers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841
56. Topics in Current Chemistry, Springer, Berlin, 2007, 274 and 275.
57. Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278
58. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 3782
59. Speziale, A. J.; Tung, C. C.; Ratts, K. W.; Yao, A. J. Am. Chem. Soc. 1965, 87, 3460
60. a table: http://evans.harvard.edu/pdf/evans-pka-table.pdf.
61. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456
62. Guzman, A.; Yuste, F.; Toscano, R. A.; Young, J. M.; Vanhorn, A. R.; Muchowski, J. M. J. Med. Chem 1986, 29, 589
63. Kleemann, A.; Engel, J.; Kutscher, B.; Faulkner, D. J.; Reichert, D. Nat. Prod. Rep. 2002, 19, 1
64. Somei, M.; Yamada Nat. Prod. Rep. 2004, 21, 278
65. Agarwal, S.; Cammerer, S.; Filali, S.; Frohner, W.; Knoll, J.; Krahl, M. P.; Reddy, K. R.; Knolker, H.-J. Curr. Org. Chem. 2005, 9, 1601
66. O'Connor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532
67. Kochanowska-Karamyam, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489
68. Cook, A. F.; Moffatt, J. G. J. Am. Chem. Soc. 1968, 90, 740
69. Daves, D., Jr.; Anderson, W. R., Jr.; Pickering, M. V. J. Chem. Soc., Chem. Commun. 1974, 301
70. Hartke, K.; Strangemann, D. Heterocycles 1986, 24, 2399
71. Fürstner, A.; Alcarazo, M.; Radkowski, K.; Lehmann, C. W. Angew. Chem., Int. Ed. 2008, 47, 8302
72. Carreño, M. C. Chem. Rev. 1995, 95, 1717
73. Bur, S. K.; Padwa, A. Chem. Rev. 2004, 104, 2401
74. Feldman, K. S. Tetrahedron 2006, 62, 5003
75. Kai, S.; Kita, Y. Topics in Current Chemistry; Springer: Berlin, 2007; Vol 274, p 35.
76. Smith, L. H. S.; Coote, S. C.; Sneddon, H. F.; Procter, D. J. Angew. Chem., Int. Ed. 2010, 49, 5832
77. Eedon, M.; Janousek, Z.; Viehe, H. G. Tetrahedron 1997, 53, 15717
78. For the process of direct α-arylation of ketones, which employs stoichiometric amount of copper of zinc salts, see: Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061
79. Macé, Y.; Blazejewski, J.-C.; Pradet, C.; Magnier, E. Eur. J. Org. Chem. 2010, 5772
80. Fascione, M. A.; Adshead, S. J.; Mandal, P. K.; Kilner, C. A.; Leach, A. G.; Turnbull, W. B. Chem.-Eur. J. 2012, 18, 2987
81. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
82. Becke, A. D. Phys. Rev. A 1988, 38, 3098
83. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
84. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
85. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327
86. Cances, E.; Mennicci, B.; Tomasi, J. Chem. Phys. 1997, 107, 3032
87. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43
88. Frisch, M. J.; Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
89. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154
90. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523
91. Grimme, S. J. Comput. Chem. 2006, 27, 1787
92. Gero, A. J. Org. Chem. 1954, 19, 469
93. Keeffe, J. R.; Kresge, A. J.; Scbepp, N. P. J. Am. Chem. Soc. 1990, 112, 4862
94. A similar intermediate has been detected by NMR and MS: Klimczyk, S.; Huang, X.; Farès, C.; Maulide, N. Org. Biomol. Chem. 2012, 10, 4327
95. Siani, G.; Angelini, G.; Maria, P. D.; Fontana, A.; Pierini, M. Org. Biomol. Chem. 2008, 6, 4236
96. Iglesias, E. New J. Chem. 2005, 29, 625
97. For an extended Pummerer reaction on an indole ring, see: Akai, S.; Kawashita, N.; Wada, Y.; Satoh, H.; Alinejad, A. H.; Kakiguchi, K.; Kuriwaki, I.; Kita, Y. Tetrahedron Lett. 2006, 47, 1881
98. Akai, S.; Morita, N.; lio, K.; Nakumura, Y.; Kita, Y. Org. Lett. 2000, 2, 2279
99. Feldman, K. S.; Vidulova, D. B. Org. Lett. 2004, 6, 1869
100. Akai, S.; Kawashita, N.; Satoh, H.; Wada, Y.; Kakiguchi, K.; Kuriwaki, I.; Kita, Y. Org. Lett. 2004, 6, 3793
101. Feldman, K. S.; Skoumbourdis, A. P. Org. Lett. 2005, 7, 929
102. Feldman, K. S.; Vidulova, D. B.; Karatjas, A. G. J. Org. Chem. 2005, 70, 6429
103. Feldman, K. S.; Karatjas, A. G. Org. Lett. 2006, 8, 4137
104. Feldman, K. S.; Fodor, M. D. J. Org. Chem. 2009, 74, 3449 and ref 20.
105. Yoshida, S.; Yorimitsu, H.; Oshima, K. Org. Lett. 2009, 11, 2185
106. Kobatake, T.; Yoshida, S.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2010, 49, 2340
107. Kobatake, T.; Fujino, D.; Yoshida, S.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2010, 132, 11838
108. Yoshida, S.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 5573
109. Yoshida, S.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2008, 37, 786
110. Eberhart, A. J.; Imbriglio, J. E.; Procter, D. J. Org. Lett. 2011, 13, 5882
111. Eberhart, A. J.; Procter, D. J. Angew. Chem., Int. Ed. 2013, 52, 4008
112. Huang, X.; Klimczyk, S.; Maulide, N. Synthesis 2012, 44, 175
113. Berger, R.; Ziller, J. W.; Van Vranken, D. L. J. Am. Chem. Soc. 1998, 120, 841
114. For similar rationale on the mechanism, see: Cuenca, A. B.; Montserrat, S.; Hossain, K. M.; Mancha, G.; Lled́s, A.; Medio-Simόn, M.; Ujaque, G.; Asensio, G. Org. Lett. 2009, 11, 4906
115. Garcia, P. G.; Lay, F.; Garcia, P. G.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363