Hydroarylation of arynes catalyzed by silver for biaryl synthesis

Journal of the American Chemical Society

Volumn 136, Issue 11, 2014, Pages 4363-4368

  Lee, Nam Kyu ^a   Yun, Sang Young ^a   Mamidipalli, Phani ^a   Salzman, Ryan M ^a   Lee, Daesung ^a   Zhou, Tao ^b   Xia, Yuanzhi ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b WENZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; SILVER;

BIARYL SYNTHESIS; BUILDING BLOCKES; DFT CALCULATION; DIELS-ALDER REACTION; ELECTROPHILIC AROMATIC SUBSTITUTIONS; HYDROARYLATION;

CATALYSIS;

BENZENE; DEUTERIUM; HYDRONIUM ION; POLYCYCLIC AROMATIC HYDROCARBON; SILVER; WATER;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; COLUMN CHROMATOGRAPHY; CYCLOADDITION; DIELS ALDER REACTION; ELECTROPHILICITY; HYDROARYLATION; ISOMER; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

ALKYNES; CATALYSIS; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE; QUANTUM THEORY; SILVER;

EID: 84896521410     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja500292x     Document Type: Article

References (75)

1. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893
2. Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563
3. Seechurn, C. C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
4. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359
5. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
6. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
7. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
8. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540
9. Kessar, S. V. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds:, Pergamon Press: New York, 1991; Vol. 4, pp 483-515.
10. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701
11. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502
12. Sanz, R. Org. Prep. Proc. Int. 2008, 40, 215-291
13. Chen, Y.; Larock, R. C. In Modern Arylation Methods; Ackermann, L., Eds.; Wiley-VCH: Weinheim, Germany, 2009.
14. Kitamura, T. Aust. J. Chem. 2010, 63, 987
15. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
16. Wu, C.; Shi, F. Asian J. Org. Chem. 2013, 2, 116
17. Huisgen, R.; Sauer, J.; Hauser, A. Chem. Ber. 1958, 91, 2366
18. Meyers, A. I.; Pansegrau, P. D. J. Chem. Soc., Chem. Commun. 1985, 690
19. Hart, H.; Harada, K.; Du, C.-J. F. J. Org. Chem. 1985, 50, 3104
20. Leroux, F.; Schlosser, M. Angew. Chem., Int. Ed. 2002, 41, 4272
21. Henderson, J. L.; Edwards, A. S.; Greaney, M. F. Org. Lett. 2007, 9, 5589
22. Liu, Z.; Larock, R. C. Angew. Chem., Int. Ed. 2007, 46, 2535
23. Becht, J.-M.; Gissot, A.; Wagner, A.; Mioskowski, C. Chem.-Eur. J. 2003, 9, 3209
24. Abboud, M.; Mamane, V.; Aubert, E.; Lecomte, C.; Fort, Y. J. Org. Chem. 2010, 75, 3224
25. Bajracharya, G. B.; Daugulis, O. Org. Lett. 2008, 10, 4625
26. Truong, T.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 4243
27. Truong, T.; Daugulis, O. Org. Lett. 2012, 14, 5964
28. Miyawaki, K.; Suzuki, R.; Kawano, T.; Ueda, I. Tetrahedron Lett. 1997, 38, 3943
29. Hoye, T. R.; Baire, B.; Niu, D.; Willoughby, P. H.; Woods, B. P. Nature 2012, 490, 208
30. Meyerson, S.; Fields, E. K. Tetrahedron Lett. 1967, 571
31. Bradley, A. Z.; Johnson, R. P. J. Am. Chem. Soc. 1997, 119, 9917
32. Kociolek, M. G.; Johnson, R. P. Tetrahedron Lett. 1999, 40, 4141
33. Kimura, H.; Torikai, K.; Miyawaki, K.; Ueda, I. Chem. Lett. 2008, 37, 662
34. Tsui, J. A.; Sterenberg, B. T. Organometallics 2009, 28, 4906
35. Ajaz, A.; Bradley, A. Z.; Burrell, R. C.; Li, W. H. H.; Daoust, K. J.; Bovee, L. B.; DiRico, K. J.; Johnson, R. P. J. Org. Chem. 2011, 76, 9320
36. Karmakar, R.; Mamidipalli, P.; Yun, S. Y.; Lee, D. Org. Lett. 2013, 15, 1938
37. Niu, D.; Willoughby, P. H.; Baire, B.; Woods, B. P.; Hoye, T. R. Nature 2013, 501, 531
38. Karmakar, R.; Yun, S. Y.; Wang, K.-P.; Lee, D. Org. Lett. 2014, 16, 6
39. Niu, D.; Hoye, T. R. Nat. Chem. 2014, 6, 34
40. Miller, R. G.; Stiles, M. J. Am. Chem. Soc. 1963, 85, 1798
41. Stiles, M.; Burckhardt, U.; Freund, G. J. Org. Chem. 1967, 32, 3718
42. Friedman, L.; Lindow, D. F. J. Am. Chem. Soc. 1968, 90, 2329
43. Brinkley, J. M.; Friedman, L. Tetrahedron Lett. 1972, 40, 4141
44. Tabushi, I.; Yamda, H.; Yoshida, Z.; Oda, R. Bull. Chem. Soc. Jpn. 1977, 50, 285
45. Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550
46. Olah, G. A. Friedel Crafts Chemistry; Wiley-Interscience: New York, 1973.
47. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
48. Foley, N. A.; Lee, J. P.; Ke, Z.; Gunnoe, T. B.; Cundari, T. R. Acc. Chem. Res. 2009, 42, 585
49. Bandini, M. Chem. Soc. Rev. 2011, 40, 1358
50. Nakao, Y. Chem. Rec. 2011, 11, 242
51. Andreatta, J. R.; McKeown, B. A.; Gunnoe, T. B. J. Organomet. Chem. 2011, 696, 305
52. Yun, S. Y.; Wang, K. P.; Lee, N.-K.; Mamidipalli, P.; Lee, D. J. Am. Chem. Soc. 2013, 135, 4668
53. Wang, K.-P.; Yun, S. Y.; Mamidipalli, P.; Lee, D. Chem. Sci. 2013, 4, 3205
54. Friedman, L. J. Am. Chem. Soc. 1967, 89, 3071
55. Crews, P.; Beard, J. J. Org. Chem. 1973, 38, 529
56. Vedejs, E.; Shepherd, R. A. Tetrahedron Lett. 1970, 11, 1863
57. Tabushi, I.; Yamda, H.; Yoshida, Z.; Oda, R. Bull. Chem. Soc. Jpn. 1977, 50, 291
58. Bennett, M. A.; Wenger, E. Chem. Ber. 1997, 130, 1029
59. Boulho, C.; Oulié, P.; Vendier, L.; Etienne, M.; Pimienta, V.; Locati, A.; Bessac, F.; Maseras, F.; Pantazis, D. A.; McGrady, J. E. J. Am. Chem. Soc. 2010, 132, 14239
60. Hassan, M. R.; Kabir, S. E.; Nicholson, B. K.; Nordlander, E.; Uddin, Md. N. Organometallics 2007, 26, 4627
61. Deaton, K. R.; Gin, M. S. Org. Lett. 2003, 5, 2477
62. Wada, K.; Pamplin, C. B.; Legzdins, P.; Patrick, B. O.; Tsyba, I.; Bau, R. J. Am. Chem. Soc. 2003, 125, 7035
63. Hughes, R. P.; Laritchev, R. B.; Williamson, A.; Incarvito, C. D.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2003, 22, 2134
64. Retbøll, M.; Edwards, A. J.; Rae, A. D.; Willis, A. C.; Bennett, M. A.; Wenger, E. J. Am. Chem. Soc. 2002, 124, 8348
65. Frid, M.; Pérez, D.; Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9469
66. Hansmann, M. H.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2013, 52, 2593
67. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735
68. Wang, X.-N.; Yeom, H.-S.; Fang, L.-C.; He, S.; Ma, Z.-X.; Kedrowski, B. L.; Hsung, R. P. Acc. Chem. Res. 2013, 47, 560
69. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
70. Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 49, 2840.
71. Goetx, A. E.; Bronner, S. M.; Cisneros, J. D.; Melamed, J. M.; Paton, R. S.; Houk, N. K.; Garg, N. K. Angew. Chem., Int. Ed. 2012, 51, 2758
72. Bronner, S. M.; Mackey, J. L.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2012, 134, 13966
73. Cheong, P. H.-Y.; Paton, R. S.; Bronner, S. M.; Im, G.-Y. J.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 1267
74. Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470
75. Shi, F.-Q.; Li, X.; Xia, Y.; Zhang, L.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 15503