Readily Removable Directing Group Assisted Chemo- and Regioselective C(sp3)-H Activation by Palladium Catalysis

Angewandte Chemie - International Edition

Volumn 54, Issue 46, 2015, Pages 13686-13690

  Zhang, Yun Fei ^a   Zhao, Hong Wei ^b   Wang, Hui ^a   Wei, Jiang Bo ^a   Shi, Zhang Jie ^a,c  

^a PEKING UNIVERSITY   (China)

^b SHANXI UNIVERSITY   (China)

^c INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

arenes; C H activation; palladium; silver; synthetic methods

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CARBONYL COMPOUNDS; CATALYSIS; CHEMICAL REACTIONS; PALLADIUM; SILVER;

ARENES; C-H ACTIVATION; DIRECTING GROUPS; FUNCTIONALIZATIONS; PALLADIUM CATALYSIS; REGIO-SELECTIVE; ROOM TEMPERATURE; SYNTHETIC METHODS;

CHEMICAL ACTIVATION;

EID: 84946488874     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201505932     Document Type: Article

References (96)

1. For recent reviews, see:
2. Handbook of C-H Transformation, Vols. 1-3 (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005;
3. "C-H activation": Topics in Current Chemistry, Vol. 292 (Eds.:, J.-Q. Yu, Z.-J. Shi,), Springer, Berlin, 2010;
4. F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826;
5. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861;
6. Y. J. Park, C.-H. Jun, Bull. Korean Chem. Soc. 2005, 26, 871;
7. K. Godula, D. Sames, Science 2006, 312, 67;
8. M. S. Chen, M. C. White, Science 2007, 318, 783;
9. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173;
10. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
11. C.-J. Li, Acc. Chem. Res. 2009, 42, 335;
12. I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890;
13. Y. Kuninobu, K. Takai, Chem. Rev. 2011, 111, 1938;
14. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068;
15. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780;
16. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 10236;
17. Angew. Chem. 2012, 124, 10382;
18. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651;
19. K. M. Engle, T. S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788.
20. 2)-H bonds, see:
21. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013;
22. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624;
23. P. Sehnal, R. J. K. Taylor, I. J. S. Fairlamb, Chem. Rev. 2010, 110, 824;
24. L.-M. Xu, B.-J. Li, Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712;
25. L. Ackermann, Chem. Commun. 2010, 46, 4866;
26. L. Ackermann, Chem. Rev. 2011, 111, 1315;
27. P.-S. Lee, T. Fujita, N. Yoshikai, J. Am. Chem. Soc. 2011, 133, 17283;
28. D. Y.-K. Chen, S. W. Youn, Chem. Eur. J. 2012, 18, 9452;
29. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960;
30. Angew. Chem. 2012, 124, 9092;
31. J. Hartwig, Acc. Chem. Res. 2012, 45, 864;
32. B. Li, P. H. Dixneuf, Chem. Soc. Rev. 2013, 42, 5744;
33. M. Wang, X. Zhang, Y.-X. Zhuang, Y. H. Xu, T.-P. Loh, J. Am. Chem. Soc. 2015, 137, 1341.
34. 3)-H bonds, see:
35. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074;
36. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654;
37. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147;
38. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885;
39. O. Baudoin, Chem. Soc. Rev. 2011, 40, 4902;
40. B.-J. Li, Z.-J. Shi, Chem. Soc. Rev. 2012, 41, 5588;
41. G. Qiu, J. Wu, Org. Chem. Front. 2015, 2, 169;
42. J. Pedroni, M. Boghi, T. Saget, N. Cramer, Angew. Chem. Int. Ed. 2014, 53, 9064;
43. Angew. Chem. 2014, 126, 9210.
44. For recent reviews, see:
45. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624;
46. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242;
47. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215;
48. J. L. Roizen, M. E. Harvey, J. Du Bois, Acc. Chem. Res. 2012, 45, 911;
49. G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 2013, 52, 11726;
50. Angew. Chem. 2013, 125, 11942;
51. L. Ackermann, Acc. Chem. Res. 2014, 47, 281;
52. A. Ros, R. Fernandez, J. M. Lassaletta, Chem. Soc. Rev. 2014, 43, 3229.
53. For a recent review, see:, Z. Huang, G. Dong, Tetrahedron Lett. 2014, 55, 5869.
54. V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154.
55. B. V. S. Reddy, L. R. Reddy, E. J. Corey, Org. Lett. 2006, 8, 3391;
56. D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965;
57. Y. Ano, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 2011, 133, 12984;
58. L. D. Tran, O. Daugulis, Angew. Chem. Int. Ed. 2012, 51, 5188;
59. Angew. Chem. 2012, 124, 5278;
60. R. K. Rit, R. Yadav, A. K. Sahoo, Org. Lett. 2012, 14, 3724;
61. Y. Xie, Y. Yang, L. Huang, X. Zhang, Y. Zhang, Org. Lett. 2012, 14, 1238;
62. R. Shang, L. Ilies, A. Matsumoto, E. Nakamura, J. Am. Chem. Soc. 2013, 135, 6030;
63. S.-Y. Zhang, Q. Li, G. He, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2013, 135, 12135;
64. R. Parella, B. Gopalakrishnan, S. A. Babu, Org. Lett. 2013, 15, 3238;
65. F. Pan, P.-X. Shen, L.-S. Zhang, X. Wang, Z.-J. Shi, Org. Lett. 2013, 15, 4758;
66. L. Ju, J. Yao, Z. Wu, Z. Liu, Y. Zhang, J. Org. Chem. 2013, 78, 10821;
67. Z. Wang, J. Ni, Y. Kuninobu, M. Kanai, Angew. Chem. Int. Ed. 2014, 53, 3496;
68. Angew. Chem. 2014, 126, 3564;
69. Y. Aihara, N. Chatani, J. Am. Chem. Soc. 2014, 136, 898;
70. X. Wu, Y. Zhao, H. Ge, J. Am. Chem. Soc. 2014, 136, 1789.
71. M. Wasa, K. S. L. Chan, X.-G. Zhang, J. He, M. Miura, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 18570;
72. J. He, S.-H. Li, Y.-Q. Deng, H.-Y. Fu, B. N. Laforteza, J. E. Spangler, A. Homs, J.-Q. Yu, Science 2014, 343, 1216;
73. S.-H. Li, G. Chen, C.-G. Feng, W. Gong, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 5267.
74. G. He, S.-Y. Zhang, W. A. Nack, Q. Li, G. Chen, Angew. Chem. Int. Ed. 2013, 52, 11124;
75. Angew. Chem. 2013, 125, 11330;
76. U. Nachbur, C. A. Stafford, A. Bankovacki, Y. Zhan, L. M. Lindqvist, B. K. Fiil, Y. Khakham, H.-J. Ko, J. J. Sandow, H. Falk, J. K. Holien, D. Chau, J. Hildebrand, J. E. Vince, P. P. Sharp, A. I. Webb, K. A. Jackman, S. Mühlen, C. L. Kennedy, K. N. Lowes, Nat. Commun. 2015, 6, 6442.
77. K. Chen, F. Hu, S.-Q. Zhang, B.-F. Shi, Chem. Sci. 2013, 4, 3906;
78. F.-J. Chen, S. Zhao, F. Hu, K. Chen, Q. Zhang, S.-Q. Zhang, B.-F. Shi, Chem. Sci. 2013, 4, 4187;
79. Q. Zhang, K. Chen, W. Rao, Y. Zhang, F.-J. Chen, B.-F. Shi, Angew. Chem. Int. Ed. 2013, 52, 13588;
80. Angew. Chem. 2013, 125, 13833.
81. S. Inoue, H. Shiota, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2009, 131, 6898;
82. N. Hasegawa, V. Charra, S. Inoue, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2011, 133, 8070.
83. For recent reviews, see:
84. D.-G. Yu, B.-J. Li, Z.-J. Shi, Acc. Chem. Res. 2010, 43, 1486;
85. B. M. Rosen, K. W. Quasdorf, D. A. Wilson, N. Zhang, A.-M. Resmerita, N. K. Garg, V. Percec, Chem. Rev. 2011, 111, 1346;
86. G. P. McGlacken, S. L. Clarke, ChemCatChem 2011, 3, 1260;
87. M. Tobisu, N. Chatani, ChemCatChem 2011, 3, 1410;
88. C. M. So, F. Y. Kwong, Chem. Soc. Rev. 2011, 40, 4963;
89. J. Yamaguchi, K. Muto, K. Itami, Eur. J. Org. Chem. 2012, 19.
90. M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680;
91. S. Li, G. Chen, C. G. Feng, W. Gong, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 5276;
92. G. He, G. Chen, Angew. Chem. Int. Ed. 2011, 50, 5192;
93. Angew. Chem. 2011, 123, 5298;
94. K. J. Stowers, K. C. Fortner, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 6541;
95. W. R. Gutekunst, R. Gianatassio, P. S. Baran, Angew. Chem. Int. Ed. 2012, 51, 7507;
96. Angew. Chem. 2012, 124, 7625.