Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis

Journal of the American Chemical Society

Volumn 137, Issue 18, 2015, Pages 5887-5890

  Dong, Zhe ^a   Wang, Jianchun ^a   Dong, Guangbin ^a  

^a The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; FUNCTIONAL GROUPS;

C-H ARYLATION; C-H FUNCTIONALIZATION; DIRECTING GROUPS; ELECTRON WITHDRAWING GROUP; REACTION CONDITIONS; SELECTIVE TRANSFORMATION; SITE SELECTIVITY; TERTIARY AMINE;

AROMATIC COMPOUNDS;

ACETIC ACID; AMINE; FUNCTIONAL GROUP; LIGAND; METAL; NORBORNENE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TERTIARY AMINE; AROMATIC HYDROCARBON; NORBORNANE DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; ARYLATION; BIOTRANSFORMATION; CATALYSIS; CATALYST; DERIVATIZATION; QUANTUM YIELD; REACTION ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINES; CATALYSIS; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE; NORBORNANES; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 84929359088     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02809     Document Type: Article

References (70)

1. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
2. Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903
3. Catellani, M.; Motti, E.; Della Ca', N. Acc. Chem. Res. 2008, 41, 1512
4. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
5. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
6. Martins, A.; Mariampillai, B.; Lautens, M. Top. Curr. Chem. 2010, 292, 1
7. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
8. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
9. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
10. Cheng, C.; Hartwig, J. F. Chem. Rev. 2015, 10.1021/cr5006414
11. Yang, J. Org. Biomol. Chem. 2015, 13, 1930
12. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R. Science 2002, 295, 305
13. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390
14. Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R. J. Am. Chem. Soc. 2003, 125, 7792
15. Murphy, J. M.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 15434
16. Cheng, C.; Hartwig, J. F. Science 2014, 343, 853
17. Cheng, C.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 592
18. Armstrong, D. R.; Clegg, W.; Dale, S. H.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 3775
19. Martínez-Martínez, A. J.; Kennedy, A. R.; Mulvey, R. E.; O'Hara, C. T. Science 2014, 346, 834
20. Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593
21. Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 463
22. Cornella, J.; Righi, M.; Larrosa, I. Angew. Chem., Int. Ed. 2011, 50, 9429
23. Luo, J.; Preciado, S.; Larrosa, I. J. Am. Chem. Soc. 2014, 136, 4109
24. Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.; Mahon, M. F.; Kociok-Köhn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133, 19298
25. Hofmann, N.; Ackermann, L. J. Am. Chem. Soc. 2013, 135, 5877
26. Leow, D.; Li, G.; Mei, T.-S.; Yu, J.-Q. Nature 2012, 486, 518
27. Dai, H.-X.; Li, G.; Zhang, X.-G.; Stepan, A. F.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 7567
28. Lee, S.; Lee, H.; Tan, K. L. J. Am. Chem. Soc. 2013, 135, 18778
29. Wan, L.; Dastbaravardeh, N.; Li, G.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 18056
30. Bera, M.; Modak, A.; Patra, T.; Maji, A.; Maiti, D. Org. Lett. 2014, 16, 5760
31. Tang, R.-Y.; Li, G.; Yu, J.-Q. Nature 2014, 507, 215
32. Yang, G.; Lindovska, P.; Zhu, D.; Kim, J.; Wang, P.; Tang, R.-Y.; Movassaghi, M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 10807
33. Deng, Y.; Yu, J.-Q. Angew. Chem. Int. Ed. 2015, 54, 888
34. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
35. Zhang, J.; Liu, Q.; Liu, X.; Zhang, S.; Jiang, P.; Wang, Y.; Luo, S.; Li, Y.; Wang, Q. Chem. Commun. 2015, 51, 1297
36. Catellani, M. Top. Organomet. Chem. 2005, 14, 21
37. Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 119
38. Motti, E.; Rossetti, M.; Bocelli, G.; Catellani, M. J. Organomet. Chem. 2004, 689, 3741
39. Mariampillai, B.; Alliot, J.; Li, M.; Lautens, M. J. Am. Chem. Soc. 2007, 129, 15372
40. Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148
41. Ferraccioli, R.; Carenzi, D.; RombolaÌ, O.; Catellani, M. Org. Lett. 2004, 6, 4759
42. Deledda, S.; Motti, E.; Catellani, M. Can. J. Chem. 2005, 83, 741
43. Motti, E.; Della Ca', N.; Deledda, S.; Fava, E.; Panciroli, F.; Catellani, M. Chem. Commun. 2010, 46, 4291
44. Maestri, G.; Della Ca', N.; Catellani, M. Chem. Commun. 2009, 4892
45. Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78
46. Wilhelm, T.; Lautens, M. Org. Lett. 2005, 7, 4053
47. Dong, Z.; Dong, G. J. Am. Chem. Soc. 2013, 135, 18350
48. Wang, X.-C.; Gong, W.; Fang, L.-Z.; Zhu, R.-Y.; Li, S.; Engle, K. M.; Yu, J.-Q. Nature 2015, 519, 334
49. Jiao, L.; Bach, T. J. Am. Chem. Soc. 2011, 133, 12990
50. Jiao, L.; Herdtweck, E.; Bach, T. J. Am. Chem. Soc. 2012, 134, 14563
51. Jiao, L.; Bach, T. Angew. Chem., Int. Ed. 2013, 52, 6080
52. Cárdenas, D. J.; Martín-Matute, B.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 5033
53. Martín-Matute, B.; Mateo, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2001, 7, 2341
54. Maestri, G.; Motti, E.; Della Ca', N.; Malacria, M.; Derat, E.; Catellani, M. J. Am. Chem. Soc. 2011, 133, 8574
55. Cope, A. C.; Friedrich, E. C. J. Am. Chem. Soc. 1968, 90, 909
56. Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666
57. Li, H.; Cai, G.-X.; Shi, Z.-J. Dalton Trans. 2010, 39, 10442
58. Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86
59. Feng, R.; Yao, J.; Liang, Z.; Liu, Z.; Zhang, Y. J. Org. Chem. 2013, 78, 3688
60. Ryabov, A. D.; Yatsimirskii, A. K. Inorg. Chem. 1984, 23, 789
61. Ryabov, A. D. Inorg. Chem. 1987, 26, 1252
62. Cooper, M. S.; Fairhurst, R. A.; Heaney, H.; Papageorgiou, G.; Wilkins, R. F. Tetrahedron 1989, 45, 1155
63. Cheng, C.; Sun, J.; Xing, L.; Xu, J.; Wang, X.; Hu, Y. J. Org. Chem. 2009, 74, 5671
64. We have synthesized the corresponding ortho- and para-arylation products. Neither of them was observed by GC analysis.
65. Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1985, 286, c13
66. Primary and secondary amines were found to be unsuitable as DGs for this transformation. The one-carbon homologue of 1a (PhCH2CH2NMe2) did not provide the desired meta-arylation product.
67. Martins, A.; Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 5186
68. Methyl 3-iodobenzoate and 3- and 4-methoxyphenyl iodide all gave low conversions (<10%) and trace amounts of products.
69. Kolesinska, B.; Kaminski, Z. J. Tetrahedron 2009, 65, 3573
70. Gong, J.-L.; Qi, X.; Wei, D.; Feng, J.-B.; Wu, X.-F. Org. Biomol. Chem. 2014, 12, 7486