Citation: Li Hua, Ren Xiangwei, Zhao Wentao, Tang Xiangyang, Wang Guangwei. Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2287-2302. doi: 10.6023/cjoc201703036 shu

Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation

a.
Department of Chemistry, School of Science, Tianjin University, Tianjin 300350
b.
Tianjin Key Laboratory of Molecular Optoelectronic Science, Tianjin 300072

Corresponding author: Zhao Wentao, wentao_zhao@tju.edu.cn Wang Guangwei, wanggw@tju.edu.cn
Received Date: 27 March 2017
Revised Date: 3 May 2017
Available Online: 17 September 2017
Fund Project: National Basic Research Program of China 2015CB856500Project supported by the National Basic Research Program of China (No. 2015CB856500) and the Natural Science Foundation of Tianjin City (No. 16JCYBJC20100)Natural Science Foundation of Tianjin City 16JCYBJC20100

Figures(20)

Transition metal-catalyzed C-H activation is one of the most important areas in organic synthesis. Directed C-H activation can obviate the prefunctionalization of substrate, therefore providing a highly efficient and concise strategy for C-C formation. The cross-coupling of transition metal-activated C-H bond with organic electrophilic reagents has been proven effective for construction of various C-C bonds. Meanwhile, the oxidative coupling between the corresponding intermediates with organometallic reagents has become the focus for chemists due to their high reactivity, and notable achievements have been made in recent years. Here the oxidative couplings of C-H bond and organometallic reagents have been discussed and summarized according to the hybridization of substrate and organometallic reagents.
- C-H activation,
- transition metal catalysis,
- directing group,
- organometallic reagents,
- C-C bond formation
1. [1]
2. [2]
3. [3]
  Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677. doi: 10.1039/b908581e
4. [4]
  Li, J.; Liu, K.; Duan, X.; Liu, J. Chin. J. Org. Chem. 2017, 37, 314(in Chinese).
5. [5]
  Gao, K.; Yoshikai, N. Acc. Chem. Res. 2014, 47, 1208. doi: 10.1021/ar400270x
6. [6]
  Su, B.; Cao, Z.-C.; Shi, Z.-J. Acc. Chem. Res. 2015, 48, 886. doi: 10.1021/ar500345f
7. [7]
  Yang, Y.; Lan, J.; You, J. Chem. Rev. 2017, 117, 8787. doi: 10.1021/acs.chemrev.6b00567
8. [8]
  (a) Dastbaravardeh, N.; Christakakou, M.; Haider, M.; Schnürch, M. Synthesis 2014, 46, 1421.
  (b) Shang, M.; Sun, S.-Z.; Wang, H.-L.; Wang, M.-M.; Dai, H.-X. Synthesis 2016, 48, 4381.
9. [9]
  Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979. doi: 10.1021/cr020377i
10. [10]
  Chen, M.; Zheng, X.; Li, W; He, J.; Lei, A. J. Am. Chem. Soc. 2010, 132, 4101. doi: 10.1021/ja100630p
11. [11]
  Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275. doi: 10.1021/ar050199q
12. [12]
  Dick, G. R.; Woerly, E. M.; Burke, M. D. Angew. Chem., Int. Ed. 2012, 51, 2667. doi: 10.1002/anie.201108608
13. [13]
  Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510. doi: 10.1021/ja0701614
14. [14]
  Wasa, M.; Chan, K. S. L.; Yu, J.-Q. Chem. Lett. 2011, 40, 1004. doi: 10.1246/cl.2011.1004
15. [15]
  Thuy-Boun, P. S.; Villa, G.; Dang, D.; Richardson, P.; Su, S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 17508. doi: 10.1021/ja409014v
16. [16]
  Neufeldt, S. R.; Seigerman, C. K.; Sanford, M. S. Org. Lett. 2013, 15, 2302. doi: 10.1021/ol400888r
17. [17]
  Peng, P.; Wang, J.; Jiang, H.; Liu, H. Org. Lett. 2016, 18, 5376. doi: 10.1021/acs.orglett.6b02755
18. [18]
  Chen, Q.; Ilies, L.; Yoshikai, N.; Nakamura, E. Org. Lett. 2011, 13, 3232. doi: 10.1021/ol2011264
19. [19]
  Ilies, L.; Ichikawa, S.; Asako, S.; Matsubara, T.; Nakamura, E. Adv. Synth. Catal. 2015, 357, 2175. doi: 10.1002/adsc.v357.10
20. [20]
  Graczyk, K.; Haven, T.; Ackermann, L. Chem.-Eur. J. 2015, 21, 8812. doi: 10.1002/chem.201501134
21. [21]
  Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 3354. doi: 10.1021/ja00479a018
22. [22]
  Xu, S.; Negishi, E. Acc. Chem. Soc. 2016, 49, 2158. doi: 10.1021/acs.accounts.6b00338
23. [23]
  Shang, R.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2015, 137, 7660. doi: 10.1021/jacs.5b04818
24. [24]
  Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78. doi: 10.1021/ja0570943
25. [25]
  Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666. doi: 10.1021/ja070588a
26. [26]
  Feng, R.; Yao, J.; Liang, Z.; Liu, Z.; Zhang, Y. J. Org. Chem. 2013, 78, 3688. doi: 10.1021/jo400186p
27. [27]
  Tan, P.-W.; Haughey, M.; Dixon, D. J. Chem. Commun. 2015, 51, 4406. doi: 10.1039/C5CC00410A
28. [28]
  Laforteza, B. N.; Chan, K. S. L.; Yu, J.-Q. Angew. Chem., Int. Ed. 2015, 54, 11143. doi: 10.1002/anie.201505204
29. [29]
  Xiao, K.-J.; Chu, L.; Chen, G.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 7796. doi: 10.1021/jacs.6b04660
30. [30]
  Krasnov, V. P.; Gruzdev, D. A.; Levit, G. L. Eur. J. Org. Chem. 2012, 1471.
31. [31]
  Vogler, T.; Studer, A. Org. Lett. 2008, 10, 129. doi: 10.1021/ol702659a
32. [32]
  Chu, J.-H.; Tsai, S.-L.; Wu, M.-J. Synthesis 2009, 3757.
33. [33]
  Ilies, L.; Okabe, J.; Yoshikai, N.; Nakamura, E. Org. Lett. 2010, 12, 2838. doi: 10.1021/ol1009448
34. [34]
  Yoshikai, N.; Asako, S.; Yamakawa, T.; Ilies, L.; Nakamura, E. Chem.-Asian J. 2011, 6, 3059. doi: 10.1002/asia.v6.11
35. [35]
  Ilies, L.; Asako, S.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 7672. doi: 10.1021/ja2017202
36. [36]
  Shang, M.; Sun, S.-Z.; Wang, H.-L.; Wang, M.-M.; Dai, H.-X. Synthesis 2016, 48, 4381. doi: 10.1055/s-0035-1562795
37. [37]
  Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154. doi: 10.1021/ja054549f
38. [38]
  Shang, R.; Ilies, L.; Asako, S.; Nakamura, E. J. Am. Chem. Soc. 2014, 136, 14349. doi: 10.1021/ja5070763
39. [39]
  Gui, Q.; Chen, X.; Hu, L.; Wang, D.; Liu, J.; Tan, Z. Adv. Synth. Catal. 2016, 358, 509. doi: 10.1002/adsc.201500884
40. [40]
  Hu, L.; Gui, Q.; Chen, X.; Tan, Z.; Zhu, G. Org. Biomol. Chem. 2016, 14, 11070. doi: 10.1039/C6OB02224C
41. [41]
  Wang, D.; Yu, X.; Xu, X.; Ge, B.; Wang, X.; Zhang, Y. Chem. Eur. J. 2016, 22, 8663. doi: 10.1002/chem.v22.25
42. [42]
  Yu, X.; Wang, D.-S.; Xu, Z.; Yang, B.; Wang, D. Org. Chem. Front. 2017, 4, 1011. doi: 10.1039/C6QO00793G
43. [43]
  (a) Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886.
  (b) Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680.
  (c) Wasa, M.; Worrell, B. T.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 1275.
  (d) Wasa, M.; Yu, J.-Q. Tetrahedron 2010, 66, 4811.
  (e) Yoo, E. J.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 17378.
  (f) Yoo, E.-J.; Ma, S.; Mei, T.-S. Chan, K. S. L. Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 7652.
44. [44]
  Wang, H.-W.; Cui, P.; Lu, Y.; Sun, W.-Y.; Yu, J.-Q. J. Org. Chem. 2016, 81, 3416. doi: 10.1021/acs.joc.6b00083
45. [45]
  (a) Leow, D.; Li, G.; Mei, T.-S.; Yu, J.-Q. Nature 2012, 486, 518.
  (b) Dai, H.-X.; Li, G.; Zhang, X.-G.; Stepan, A. F.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 7567.
46. [46]
  Wan, L.; Dastbaravardeh, N.; Li, G.; Yu, J-Q. J. Am. Chem. Soc. 2013, 135, 18056. doi: 10.1021/ja410760f
47. [47]
  Chinnagolla, R. K.; Jeganmohan, M. Org. Lett. 2012, 14, 5246. doi: 10.1021/ol3024067
48. [48]
  (a) Chinnagolla, R. K.; Jeganmohan, M. Chem. Commun. 2014, 50, 2442.
  (b) Hubrich, J.; Himmler, T.; Rodefeld, L.; Ackermanna, L. Adv. Synth. Catal. 2015, 357, 474.
49. [49]
  Nishikata, T.; Abela, A. R.; Huang, S.; Lipshutz, B. H. J. Am. Chem. Soc. 2010, 132, 4978. doi: 10.1021/ja910973a
50. [50]
  Shang, M.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. Org. Lett. 2014, 16, 5666. doi: 10.1021/ol5027377
51. [51]
  (a) Zhou, H.; Xu, Y.-H.; Chung, W.-J.; Loh, T.-P. Angew. Chem., Int. Ed. 2009, 48, 5355.
  (b) Li, W.; Yin, Z.; Jiang, X.; Sun, P. J. Org. Chem. 2011, 76, 8543.
52. [52]
  Zhao, S.; Liu, B.; Zhan, B.-B.; Zhang, W.-D.; Shi, B.-F. Org. Lett. 2016, 18, 4586. doi: 10.1021/acs.orglett.6b02236
53. [53]
  Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698. doi: 10.1021/ja029273f
54. [54]
  Ueno, S.; Chatani, N.; Kakiuchi, F. J. Org. Chem. 2007, 72, 3600. doi: 10.1021/jo070182g
55. [55]
  Paymode, D. J.; Ramana, C. V. J. Org. Chem. 2015, 80, 11551. doi: 10.1021/acs.joc.5b01932
56. [56]
  Tiwari, V. K.; Kamal, N.; Kapur, M. Org. Lett. 2017, 19, 262. doi: 10.1021/acs.orglett.6b03558
57. [57]
  Yang, Y.; Qiu, X.; Zhao, Y.; Mu, Y.; Shi, Z. J. Am. Chem. Soc. 2016, 138, 495. doi: 10.1021/jacs.5b11569
58. [58]
  Wang, L.; Li, Z.; Qu, X.; Peng, W. Chin. J. Chem. 2015, 33, 1015. doi: 10.1002/cjoc.201500354
59. [59]
  Wang, D.-H.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 17676. doi: 10.1021/ja806681z
60. [60]
  Engle, K. M.; Thuy-Boun, P. S.; Dang, M.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 18183. doi: 10.1021/ja203978r
61. [61]
  (a) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
  (b) Samanta, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2011, 50, 5217.
  (c) Yu, M.; Xie, Y.; Xie, C.; Zhang, Y. Org. Lett. 2012, 14, 2164.
  (d) Wang, D.; Yu, X.; Yao, W.; Hu, W.; Ge, C.; Shi, X. Chem.-Eur. J. 2016, 22, 5543.
62. [62]
  Yao, J.; Yu, M.; Zhang, Y. Adv. Synth. Catal. 2012, 354, 3205. doi: 10.1002/adsc.201200447
63. [63]
  Wang, J.; Wang, S.; Wang, G.; Zhang, J.; Yu, X.-Q. Chem. Commun. 2012, 48, 11769. doi: 10.1039/c2cc35468c
64. [64]
  Wang, D.; Ge, B.; Li, L.; Shan, J.; Ding, Y. J. Org. Chem. 2014, 79, 8607. doi: 10.1021/jo501467v
65. [65]
  Ge, B.; Wang, D.; Dong, W.; Ma, P.; Li, Y.; Ding, Y. Tetrahedron Lett. 2014, 55, 5443. doi: 10.1016/j.tetlet.2014.08.023
66. [66]
  Wang, D.; Yu, X.; Ge, B.; Miao, H.; Ding, Y. Chin. J. Org. Chem. 2015, 35, 676. doi: 10.6023/cjoc201412047
67. [67]
  Liu, C.; Yang, F. Chin. J. Chem. 2016, 34, 1213. doi: 10.1002/cjoc.v34.12
68. [68]
  Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780. doi: 10.1021/ja501910e
69. [69]
  Landge, V. G.; Midya, S. P.; Rana, J.; Shinde, D. R.; Balaraman, E. Org. Lett. 2016, 18, 5252. doi: 10.1021/acs.orglett.6b02549
70. [70]
  Arndtsen, B. A.; Bergman, R.; Mobley, T. A.; Peterson, T. Acc. Chem. Res. 1995, 28, 154. doi: 10.1021/ar00051a009
71. [71]
  Zhao, J.-B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235(in Chinese).
72. [72]
  Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634. doi: 10.1021/ja0646747
73. [73]
  Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190. doi: 10.1021/ja801355s
74. [74]
  Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598. doi: 10.1021/ja207607s
75. [75]
  (a) Bachrach, S. M. J. Org. Chem. 2008, 73, 2466.
  (b) Li, S.; Zhu, R.-Y.; Xiao, K.-J.; Yu, J.-Q. Angew. Chem., Int. Ed. 2016, 55, 4317.
76. [76]
  Xiao, K.-J.; Lin, D. W.; Miura, M.; Zhu, R.-Y.; Gong, W.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 8138. doi: 10.1021/ja504196j
77. [77]
  Wang, X.; Yu, D.-G.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 10280. doi: 10.1002/anie.201503888
78. [78]
  (a) Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220.
  (b) Phani Kumar, N. Y.; Jeyachandran, R.; Ackermann, L. J. Org. Chem. 2013, 78, 4145.
  (c) Dastbaravardeh, N.; Schnürch, M.; Mihovilovic, M. D. Org. Lett. 2012, 14, 1930.
79. [79]
  Spangler, J. E.; Kobayashi, Y.; Verma, P.; Wang, D.-H.; Yu, J.-Q. J.Am. Chem. Soc. 2015, 137, 11876. doi: 10.1021/jacs.5b06740
80. [80]
  (a) He, G.; Zhao, Y.; Zhang, S.; Lu, C.-X.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3.
  (b) Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.-S.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124.
81. [81]
  Chan, K. S. L.; Wasa, M.; Chu, L.; Laforteza, B. N.; Miura, M.; Yu, J.-Q. Nat. Chem. 2014, 6, 146. doi: 10.1038/nchem.1836
82. [82]
  Yuan, C.; Tu, G.; Zhao, Y. Org. Lett. 2017, 19, 356. doi: 10.1021/acs.orglett.6b03522
83. [83]
  He, J.; Takise, R.; Fu, H.; Yu, J.-Q. J. Am. Chem. Soc. 2015, 137, 4618. doi: 10.1021/jacs.5b00890
84. [84]
  He, J.; Li, S.; Deng, Y.; Fu, H.; Laforteza, B. N.; Spangler, J. E.; Homs, A.; Yu, J.-Q. Science 2014, 343, 1216. doi: 10.1126/science.1249198
85. [85]
  He, C.; Gaunt, M. J. Angew. Chem., Int. Ed. 2015, 54, 15840. doi: 10.1002/anie.201508912
86. [86]
  McNally, A.; Haffemayer, B.; Collins, B. S. L.; Gaunt, M. J. Nature 2014, 510, 129. doi: 10.1038/nature13389
87. [87]
  Smalley, A. P.; Gaunt, M. J. J. Am. Chem. Soc. 2015, 137, 10632. doi: 10.1021/jacs.5b05529
88. [88]
  Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030. doi: 10.1021/ja402806f
89. [89]
  Gu, Q.; Al Mamari, H. H.; Graczyk, K.; Diers, E.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 3868. doi: 10.1002/anie.201311024
90. [90]
  Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984. doi: 10.1021/ja206002m
91. [91]
  Luo, F-X.; Xu, X.; Wang, D.; Cao, Z.-C.; Zhang, Y.-F.; Shi, Z.-J. Org. Lett. 2016, 18, 2040. doi: 10.1021/acs.orglett.6b00289
92. [92]
  Luo, F.-X.; Cao, Z.-C.; Zhao, H.-W.; Wang, D.; Zhang, Y.-F.; Xu, X.; Shi, Z.-J. Organometallics 2017, 36, 18. doi: 10.1021/acs.organomet.6b00529
93. [93]
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