Ortho vs ipso: Site-selective pd and norbornene-catalyzed arene c-h amination using aryl halides

Journal of the American Chemical Society

Volumn 135, Issue 49, 2013, Pages 18350-18353

  Dong, Zhe ^a   Dong, Guangbin ^a  

^a University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; C-H AMINATION; C-H FUNCTIONALIZATION; ISO-PROPANOLS; REDUCTANTS; SITE SELECTIVE; SITE SELECTIVITY;

AMINES; CATALYSIS; FUNCTIONAL GROUPS;

METAL HALIDES;

HALIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON;

AMINATION; ARTICLE; CATALYST; CONTROLLED STUDY; ELECTROPHILICITY; IODINATION; PROTON TRANSPORT; SYNTHESIS;

AMINATION; BORON COMPOUNDS; CARBON; HALOGENS; HYDROGEN; PALLADIUM;

EID: 84890522186     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja410823e     Document Type: Article

References (92)

1. Cheng, J.; Kamiya, K.; Kodama, I. Cardiovasc. Drug Rev. 2001, 19, 152
2. Sànchez, C.; Mèndez, C.; Salas, J. A. Nat. Prod. Rep. 2006, 23, 1007
3. Barker, T. J.; Jarvo, E. R. Synthesis 2011, 2011, 3954
4. Buncel, E.; Dust, J. M.; Terrier, F. Chem. Rev. 1995, 95, 2261
5. Ma̧kosza, M.; Wojciechowski, K. Chem. Rev. 2004, 104, 2631
6. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
7. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
8. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
9. Engle, K. M.; Mei, T.-S.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 1478
10. Hartwig, J. F.; Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
11. Jiang, L.; Buchwald, S. L. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
12. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534
13. Maiti, D.; Fors, B. P.; Henderson, J. L.; Nakamura, Y.; Buchwald, S. L. Chem. Sci. 2011, 2, 57
14. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27
15. Aubin, Y.; Fischmeister, C.; Thomas, C. M.; Renaud, J.-L. Chem. Soc. Rev. 2010, 39, 4130
16. Maimone, T. J.; Milner, P. J.; Kinzel, T.; Zhang, Y.; Takase, M. K.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 18106
17. Milner, P. J.; Maimone, T. J.; Su, M.; Chen, J.; Müller, P.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 19922
18. Shrestha, R.; Mukherjee, P.; Tan, Y.; Litman, Z. C.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 8480
19. Boursalian, G. B.; Ngai, M.-Y.; Hojczyk, K. N.; Ritter, T. J. Am. Chem. Soc. 2013, 135, 13278
20. Kantak, A. A.; Potavathri, S.; Barham, R. A.; Romano, K. M.; DeBoef, B. J. Am. Chem. Soc. 2011, 133, 19960
21. Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382
22. Lubriks, D.; Sokolovs, I.; Suna, E. J. Am. Chem. Soc. 2012, 134, 15436
23. Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048
24. Mei, T.-S.; Wang, X.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 10806
25. Ng, K.-H.; Chan, A. S. C.; Yu, W.-Y. J. Am. Chem. Soc. 2010, 132, 12862
26. He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2011, 134, 3
27. Kim, J. Y.; Park, S. H.; Ryu, J.; Cho, S. H.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2012, 134, 9110
28. Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 9904
29. Ryu, J.; Kwak, J.; Shin, K.; Lee, D.; Chang, S. J. Am. Chem. Soc. 2013, 135, 12861
30. Shin, K.; Baek, Y.; Chang, S. Angew. Chem., Int. Ed. 2013, 52, 8031
31. Thirunavukkarasu, V. S.; Raghuvanshi, K.; Ackermann, L. Org. Lett. 2013, 15, 3286
32. Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem. 2013, 125, 6159
33. Yu, S.; Wan, B.; Li, X. Org. Lett. 2013, 15, 3706
34. Zhao, H.; Shang, Y.; Su, W. Org. Lett. 2013, 15, 5106
35. Catellani, M. Top. Organomet. Chem. 2005, 14, 21
36. Martins, A.; Mariampillai, B.; Lautens, M. Top. Curr. Chem. 2010, 292, 1
37. Ferraccioli, R. Synthesis 2013, 45, 581
38. Catellani, M.; Motti, E.; Della Ca', N. Acc. Chem. Res. 2008, 41, 1512
39. Candito, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 6713
40. Gerick, K. M.; Chai, D. I.; Bieler, N.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 1447
41. Maestri, G.; Della Ca', N.; Catellani, M. Chem. Commun. 2009, 4892
42. Zhao, Y. B.; Mariampillai, B.; Candito, D. A.; Laleu, B.; Li, M. Z.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 1849
43. Motti, E.; Della Ca', N.; Deledda, S.; Fava, E.; Panciroli, F.; Catellani, M. Chem. Commun. 2010, 46, 4291
44. Blanchot, M.; Candito, D. A.; Larnaud, F.; Lautens, M. Org. Lett. 2011, 13, 1486
45. Jiao, L.; Bach, T. J. Am. Chem. Soc. 2011, 133, 12990
46. Jiao, L.; Herdtweck, E.; Bach, T. J. Am. Chem. Soc. 2012, 134, 14563
47. Jiao, L.; Bach, T. Angew. Chem., Int. Ed. 2013, 52, 6080
48. Sui, X.; Zhu, R.; Li, G.; Ma, X.; Gu, Z. J. Am. Chem. Soc. 2013, 135, 9318
49. Catellani, M.; Mann, B. E. J. Organomet. Chem. 1990, 390, 251
50. Bocelli, G.; Catellani, M.; Ghelli, S. J. Organomet. Chem. 1993, 458, C12
51. Cárdenas, D. J.; Martín-Matute, B.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 5033
52. Martín-Matute, B.; Mateo, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2001, 7, 2341
53. Maestri, G.; Motti, E.; Della Ca', N.; Malacria, M.; Derat, E.; Catellani, M. J. Am. Chem. Soc. 2011, 133, 8574
54. Chai, D. I.; Thansandote, P.; Lautens, M. Chem.-Eur. J. 2011, 17, 8175
55. Deledda, S.; Motti, E.; Catellani, M. Can. J. Chem. 2005, 83, 741
56. Wilhelm, T.; Lautens, M. Org. Lett. 2005, 7, 4053
57. Mitsudo, K.; Thansandote, P.; Wilhelm, T.; Mariampillai, B.; Lautens, M. Org. Lett. 2006, 8, 3939
58. Martins, A.; Lautens, M. Org. Lett. 2008, 10, 5095
59. Martins, A.; Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 5186
60. Motti, E.; Ca', N. D.; Xu, D.; Piersimoni, A.; Bedogni, E.; Zhou, Z.-M.; Catellani, M. Org. Lett. 2012, 14, 5792
61. Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. 1997, 36, 119
62. Motti, E.; Rossetti, M.; Bocelli, G.; Catellani, M. J. Organomet. Chem. 2004, 689, 3741
63. Mariampillai, B.; Alliot, J.; Li, M.; Lautens, M. J. Am. Chem. Soc. 2007, 129, 15372
64. Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148
65. Ferraccioli, R.; Carenzi, D.; Rombolà, O.; Catellani, M. Org. Lett. 2004, 6, 4759
66. Berman, A. M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680
67. Berman, A. M.; Johnson, J. S. Synlett 2005, 2005, 1799
68. Campbell, M. J.; Johnson, J. S. Org. Lett. 2007, 9, 1521
69. Barker, T. J.; Jarvo, E. R. J. Am. Chem. Soc. 2009, 131, 15598
70. Barker, T. J.; Jarvo, E. R. Angew. Chem., Int. Ed. 2011, 50, 8325
71. Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. Angew. Chem., Int. Ed. 2012, 51, 3953
72. Xiao, Q.; Tian, L.; Tan, R.; Xia, Y.; Qiu, D.; Zhang, Y.; Wang, J. Org. Lett. 2012, 14, 4230
73. Hendrick, C. E.; McDonald, S. L.; Wang, Q. Org. Lett. 2013, 15, 3444
74. Brunel, J. M.; Heumann, A.; Buono, G. Angew. Chem., Int. Ed. 2000, 39, 1946
75. Storsberg, J.; Nandakumar, M. V.; Sankaranarayanan, S.; Kaufmann, D. E. Adv. Synth. Catal. 2001, 343, 177
76. Zhong, J.; Xie, J.-H.; Wang, A.-E.; Zhang, W.; Zhou, Q.-L. Synlett 2006, 2006, 1193
77. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
78. Yoo, E. J.; Ma, S.; Mei, T.-S.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 7652
79. Shang, M.; Zeng, S.-H.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. Org. Lett. 2013, 15, 5286
80. Grohmann, C.; Wang, H.; Glorius, F. Org. Lett. 2013, 15, 3014
81. For a review series on hydride-transfer reactions, see: Krische, M. J.; Sun, Y. Acc. Chem. Res. 2007, 40, 1237
82. Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 132, 6900
83. Ng, K.-H.; Zhou, Z.; Yu, W.-Y. Org. Lett. 2012, 14, 272
84. Grohmann, C.; Wang, H.; Glorius, F. Org. Lett. 2012, 14, 656
85. Ng, K.-H.; Zhou, Z.; Yu, W.-Y. Chem. Commun. 2013, 49, 7031
86. In the absence of Pd (entry 2), 2a was found fully consumed by the base; also see: Li, G.; Qian, S.; Wang, C.; You, J. Angew. Chem., Int. Ed. 2013, 52, 7837
87. For a monoalkylated Catellani reaction product, see: Rudolph, A.; Rackelmann, N.; Turcotte-Savard, M.-O.; Lautens, M. J. Org. Chem. 2009, 74, 289
88. Kroutil, J.; Trnka, T.; Cerny, M. Org. Lett. 2000, 2, 1681
89. Cheng, C.; Sun, J.; Xing, L.; Xu, J.; Wang, X.; Hu, Y. J. Org. Chem. 2009, 74, 5671
90. Neel, A. K.; Charles, B. M. U.S. Patent 013860, Dec 15, 2005.
91. For synthesis of 6a and 6b by iodination, see: Zhou, C.-Y.; Li, J.; Peddibhotla, S.; Romo, D. Org. Lett. 2010, 12, 2104
92. For selective synthesis of 8, see: Murphy, J. M.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 15434