Citation: Lu Xi, He Shi-Jiang, Cheng Wan-Min, Shi Jing. Transition-metal-catalyzed C-H functionalization for late-stage modification of peptides and proteins[J]. Chinese Chemical Letters, ;2018, 29(7): 1001-1008. doi: 10.1016/j.cclet.2018.05.011 shu

Transition-metal-catalyzed C-H functionalization for late-stage modification of peptides and proteins

Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China, Hefei 230026, China

Corresponding author: Shi Jing, shijing@ustc.edu.cn
Received Date: 23 March 2018
Revised Date: 17 April 2018
Accepted Date: 18 April 2018
Available Online: 5 July 2018

Figures(23)

Late-stage modification of peptides and proteins meets the increasing demand in biochemical and pharmaceutical communities. These modification strategies could provide functionalized nonproteinogenic analogues with enhanced biological activities or improved therapeutic capabilities compared to their natural counterparts. Recent years, transition-metal-promoted functionalization of ubiquitous C-H bonds has been emerged as a powerful and tunable tool in this area, both for backbone diversifications and labeling of specific moieties. These reactions were flexible and expedient in both academic and industrial laboratories, especially considering their atom and step-economy, good functional group compatibility, accurate site selectivity. This review surveys the progress achieved in the late-stage modification of peptides and proteins utilizing transition-metal-catalyzed C-H functionalization with C-C and C-X (F, Cl, O, N, B, etc.) bonds formation.
- Transition-metals,
- C-H functionalization,
- Chemo-and site selective,
- Late-stage modification,
- Peptides and proteins
1. [1]
  K. Fosgerau, T. Hoffmann, Drug Discov. Today 20(2015) 122-128. doi: 10.1016/j.drudis.2014.10.003
2. [2]
  B. Albada, N. Metzler-Nolte, Chem. Rev. 116(2016) 11797-11839. doi: 10.1021/acs.chemrev.6b00166
3. [3]
  T. Uhlig, T. Kyprianou, F.G. Martinelli, et al., EuPA Open Proteom. 4(2014) 58-69. doi: 10.1016/j.euprot.2014.05.003
4. [4]
  A.A. Kaspar, J.M. Reichert, Drug Discov. Today 18(2013) 807-817. doi: 10.1016/j.drudis.2013.05.011
5. [5]
  D.J. Craik, D.P. Fairlie, S. Liras, et al., Chem. Biol. Drug. Des. 81(2013) 136-147. doi: 10.1111/cbdd.2012.81.issue-1
6. [6]
  N. Krall, F.P. da Cruz, O. Boutureira, et al., Nat. Chem. 8(2015) 103-113.
7. [7]
  M. Yang, J. Li, P.R. Chen, Chem. Soc. Rev. 43(2014) 6511-6526. doi: 10.1039/C4CS00117F
8. [8]
  K. Lang, J.W. Chin, Chem. Rev. 114(2014) 4764-4806. doi: 10.1021/cr400355w
9. [9]
  Y. Gong, L. Pan, Tetrahedron Lett. 56(2015) 2123-2132. doi: 10.1016/j.tetlet.2015.03.065
10. [10]
  X. Chen, Y.W. Wu, Org. Biomol. Chem. 14(2016) 5417-5439. doi: 10.1039/C6OB00126B
11. [11]
  H. Liu, X. Li, Acta Chim. Sinica 72(2014) 1197-1198. doi: 10.6023/A14110820
12. [12]
  J.B. Li, S. Tang, J.S. Zheng, et al., Acc. Chem. Res. 50(2017) 1143-1153. doi: 10.1021/acs.accounts.7b00001
13. [13]
  Y. Lin, J. Wang, Y. Lu, Sci. China Chem. 57(2014) 346-355. doi: 10.1007/s11426-014-5063-5
14. [14]
  H.K. Cui, Y. Guo, Y. He, et al., Angew. Chem. Int. Ed. 52(2013) 9558-9562. doi: 10.1002/anie.v52.36
15. [15]
  J.M. Chalker, G.J.L. Bernardes, B.G. Davis, Acc. Chem. Res. 44(2011) 730-741. doi: 10.1021/ar200056q
16. [16]
  J. Altenbuchner, M. Siemann-Herzberg, C. Syldatk, Curr. Opin. Biotechnol. 12(2001) 559-563. doi: 10.1016/S0958-1669(01)00263-4
17. [17]
  H. Xiao, A. Chatterjee, S.H. Choi, et al., Angew. Chem. Int. Ed. 52(2013) 14080-14083. doi: 10.1002/anie.201308137
18. [18]
  Y. Huang, L. Liu, Sci. China Chem. 58(2015) 1779-1781.
19. [19]
  Q.Q. He, G.M. Fang, L. Liu, Chin. Chem. Lett. 24(2013) 265-269. doi: 10.1016/j.cclet.2013.03.013
20. [20]
  X. Wang, X. Wang, J. Hu, et al., Acta Chim. Sinica 73(2015) 699-704. doi: 10.6023/A15030205
21. [21]
  C.Z. Tao, Z.T. Zhang, J.W. Wu, et al., Chin. Chem. Lett. 25(2014) 532-534. doi: 10.1016/j.cclet.2014.01.035
22. [22]
  F. Ni, C. Fu, X. Gao, et al., Sci. China Chem. 58(2015) 374-382. doi: 10.1007/s11426-015-5321-1
23. [23]
  S.B.H. Kent, Annu. Rev. Biochem. 57(1988) 957-989. doi: 10.1146/annurev.bi.57.070188.004521
24. [24]
  P. Dawson, T. Muir, I. Clark-Lewis, et al., Science 266(1994) 776-779. doi: 10.1126/science.7973629
25. [25]
  S.B.H. Kent, Chem. Soc. Rev. 38(2009) 338-351. doi: 10.1039/B700141J
26. [26]
  G.M. Fang, Y.M. Li, F. Shen, et al., Angew. Chem. Int. Ed. 50(2011) 7645-7649. doi: 10.1002/anie.201100996
27. [27]
  G.M. Fang, J.X. Wang, L. Liu, Angew. Chem. Int. Ed. 51(2012) 10347-10350. doi: 10.1002/anie.201203843
28. [28]
  Z. Wang, W. Xu, L. Liu, et al., Nat. Chem. 8(2016) 698-704. doi: 10.1038/nchem.2517
29. [29]
  M. Pan, S. Gao, Y. Zheng, et al., J. Am. Chem. Soc. 138(2016) 7429-7435. doi: 10.1021/jacs.6b04031
30. [30]
  C.D. Spicer, B.G. Davis, Nat. Commun. 5(2014) 4740. doi: 10.1038/ncomms5740
31. [31]
  O. Boutureira, G.J.L. Bernardes, Chem. Rev. 115(2015) 2174-2195. doi: 10.1021/cr500399p
32. [32]
  T.W. Lyons, M.S. Sanford, Chem. Rev. 110(2010) 1147-1169. doi: 10.1021/cr900184e
33. [33]
  T. Gensch, M.N. Hopkinson, F. Glorius, et al., Chem. Soc. Rev. 45(2016) 2900-2936. doi: 10.1039/C6CS00075D
34. [34]
  H. Sun, N. Guimond, Y. Huang, Org. Biomol. Chem. 14(2016) 8389-8397. doi: 10.1039/C6OB01258B
35. [35]
  K.M. Engle, T.S. Mei, M. Wasa, et al., Acc. Chem. Res. 45(2012) 788-802. doi: 10.1021/ar200185g
36. [36]
  Y. Segawa, T. Maekawa, K. Itami, Angew. Chem. Int. Ed. 54(2015) 66-81. doi: 10.1002/anie.201403729
37. [37]
  G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 52(2013) 11726-11743. doi: 10.1002/anie.v52.45
38. [38]
  W. Ma, P. Gandeepan, J. Li, et al., Org. Chem. Front. 4(2017) 1435-1467. doi: 10.1039/C7QO00134G
39. [39]
  Q.Z. Zheng, N. Jiao, Chem. Soc. Rev. 45(2016) 4590-4627. doi: 10.1039/C6CS00107F
40. [40]
  P. Tao, Y. Jia, Sci. China Chem. 59(2016) 1109-1125. doi: 10.1007/s11426-016-0058-7
41. [41]
  K. Wang, F. Hu, Y. Zhang, et al., Sci. China Chem. 58(2015) 1252-1265. doi: 10.1007/s11426-015-5362-5
42. [42]
  X. Yang, G. Shan, L. Wang, et al., Tetrahedron Lett. 57(2016) 819-836. doi: 10.1016/j.tetlet.2016.01.009
43. [43]
  Y. Rao, G. Shan, X. Yang, Sci. China Chem. 57(2014) 930-944.
44. [44]
  J. Wang, Sci. China Chem. 57(2014) 1057.
45. [45]
  Z. Wang, P. Xie, Y. Xia, Chin. Chem. Lett. 29(2018) 47-53. doi: 10.1016/j.cclet.2017.06.018
46. [46]
  M.E. Wei, L.H. Wang, Y.D. Li, et al., Chin. Chem. Lett. 26(2015) 1336-1340. doi: 10.1016/j.cclet.2015.08.009
47. [47]
  J. Ding, Y. Guo, L.Y. Shao, et al., Chin. Chem. Lett. 27(2016) 1617-1621. doi: 10.1016/j.cclet.2016.04.007
48. [48]
  L. Xiang, K. Yang, Q.L. Song, Chin. Chem. Lett. 28(2017) 517-520. doi: 10.1016/j.cclet.2016.11.023
49. [49]
  Y.Y. Jiang, X. Man, S. Bi, Sci. China Chem. 59(2016) 1448-1466. doi: 10.1007/s11426-016-0330-3
50. [50]
  Z.Y. Xu, H.Z. Yu, Y. Fu, Sci. China Chem. 60(2017) 165-166.
51. [51]
  Y. Wang, H. Zhou, K. Xu, et al., Chin. Chem. Lett. 28(2017) 92-96. doi: 10.1016/j.cclet.2016.05.011
52. [52]
  D. Zhou, C. Wang, M. Li, et al., Chin. Chem. Lett. 29(2018) 191-193. doi: 10.1016/j.cclet.2017.06.007
53. [53]
  T.J. Gong, B. Xiao, W.M. Cheng, et al., J. Am. Chem. Soc. 135(2013) 10630-10633. doi: 10.1021/ja405742y
54. [54]
  B. Xiao, Z.J. Liu, L. Liu, et al., J. Am. Chem. Soc. 135(2013) 616-619. doi: 10.1021/ja3113752
55. [55]
  J.F. Hartwig, M.A. Larsen, ACS Central Sci. 2(2016) 281-292. doi: 10.1021/acscentsci.6b00032
56. [56]
  J. Wencel-Delord, F. Glorius, Nat. Chem. 5(2013) 369-375. doi: 10.1038/nchem.1607
57. [57]
  M. Jbara, S.K. Maity, A. Brik, Angew. Chem. Int. Ed. 56(2017) 10644-10655. doi: 10.1002/anie.201702370
58. [58]
  D.Y. Chen, S.W. Youn, Chem. Eur. J. 18(2012) 9452-9474. doi: 10.1002/chem.201201329
59. [59]
  Y. Liang, N. Jiao, Sci. China Chem. 60(2017) 105-106. doi: 10.1007/s11426-016-0441-6
60. [60]
  H. Yan, C. Zhu, Sci. China Chem. 60(2017) 214-222. doi: 10.1007/s11426-016-0399-5
61. [61]
  Y. Hu, C. Wang, Sci. China Chem. 59(2016) 1301-1305. doi: 10.1007/s11426-016-0164-8
62. [62]
  J. Ruiz-Rodriguez, F. Albericio, R. Lavilla, Chem. Eur. J. 16(2010) 1124-1127. doi: 10.1002/chem.v16:4
63. [63]
  H. Dong, C. Limberakis, S. Liras, et al., Chem. Commun. 48(2012) 11644-11646. doi: 10.1039/c2cc36962a
64. [64]
  L. Mendive-Tapia, S. Preciado, J. García, et al., Nat. Commun. 6(2015) 7160. doi: 10.1038/ncomms8160
65. [65]
  L. Mendive-Tapia, A. Bertran, J. García, et al., Chem. Eur. J. 22(2016) 13114-13119. doi: 10.1002/chem.201601832
66. [66]
  T.J. Williams, A.J. Reay, A.C. Whitwood, et al., Chem. Commun. 50(2014) 3052-3054. doi: 10.1039/C3CC48481E
67. [67]
  A.J. Reay, T.J. Williams, I.J.S. Fairlamb, Org. Biomol. Chem. 13(2015) 8298-8309. doi: 10.1039/C5OB01174D
68. [68]
  Y. Zhu, M. Bauer, L. Ackermann, Chem. Eur. J. 21(2015) 9980-9983. doi: 10.1002/chem.201501831
69. [69]
  A.J. Reay, L.A. Hammarback, J.T.W. Bray, et al., ACS Catal. 7(2017) 5174-5179. doi: 10.1021/acscatal.6b03121
70. [70]
  Y. Zhu, M. Bauer, J. Ploog, et al., Chem. Eur. J. 20(2014) 13099-13102. doi: 10.1002/chem.201404603
71. [71]
  A. Schischko, H. Ren, N. Kaplaneris, et al., Angew. Chem. Int. Ed. 56(2017) 1576-1580. doi: 10.1002/anie.201609631
72. [72]
  A.F.M. Noisier, M.A. Brimble, Chem. Rev. 114(2014) 8775-8806. doi: 10.1021/cr500200x
73. [73]
  X. Lu, B. Xiao, R. Shang, et al., Chin. Chem. Lett. 27(2016) 305-311. doi: 10.1016/j.cclet.2015.12.021
74. [74]
  Y. Dang, S. Qu, J.W. Nelson, et al., J. Am. Chem. Soc. 137(2015) 2006-2014. doi: 10.1021/ja512374g
75. [75]
  M. Fan, D. Ma, Angew. Chem. Int. Ed. 52(2013) 12152-12155. doi: 10.1002/anie.201306583
76. [76]
  B. Mondal, B. Roy, U. Kazmaier, J. Org. Chem. 81(2016) 11646-11655. doi: 10.1021/acs.joc.6b01963
77. [77]
  M. Bauer, W. Wang, M.M. Lorion, et al., Angew. Chem. Int. Ed. 57(2018) 203-207. doi: 10.1002/anie.201710136
78. [78]
  W. Gong, G. Zhang, T. Liu, et al., J. Am. Chem. Soc. 136(2014) 16940-16946. doi: 10.1021/ja510233h
79. [79]
  A.F.M. Noisier, J. García, I.A. IonuÛ, et al., Angew. Chem. Int. Ed. 56(2017) 314-318. doi: 10.1002/anie.201608648
80. [80]
  J. Tang, Y. He, H. Chen, et al., Chem. Sci. 8(2017) 4565-4570. doi: 10.1039/C6SC05530C
81. [81]
  S. Zhu, M. Rueping, Chem. Commun. 48(2012) 11960-11962. doi: 10.1039/c2cc36995h
82. [82]
  M. San Segundo, I. Guerrero, A. Correa, Org. Lett. 19(2017) 5288-5291. doi: 10.1021/acs.orglett.7b02567
83. [83]
  X. Wu, D. Zhang, S. Zhou, et al., Chem. Commun. 51(2015) 12571-12573. doi: 10.1039/C5CC03706A
84. [84]
  L. Zhao, O. Baslé, C.J. Li, Proc. Nat. Acad. Sci. 106(2009) 4106-4111. doi: 10.1073/pnas.0809052106
85. [85]
  L.D. Tran, O. Daugulis, Angew. Chem. Int. Ed. 51(2012) 5188-5191. doi: 10.1002/anie.201200731
86. [86]
  S.M. Ametamey, M. Honer, P.A. Schubiger, Chem. Rev. 108(2008) 1501-1516. doi: 10.1021/cr0782426
87. [87]
  K. Chen, F. Hu, S.Q. Zhang, et al., Chem. Sci. 4(2013) 3906-3911. doi: 10.1039/c3sc51747k
88. [88]
  K. Chen, B.F. Shi, Angew. Chem. Int. Ed. 53(2014) 11950-11954. doi: 10.1002/anie.201407848
89. [89]
  S.Y. Zhang, Q. Li, G. He, et al., J. Am. Chem. Soc. 135(2013) 12135-12141. doi: 10.1021/ja406484v
90. [90]
  Q. Yang, S.D. Yang, ACS Catal. 7(2017) 5220-5224. doi: 10.1021/acscatal.7b01779
91. [91]
  S.Y. Zhang, G. He, W.A. Nack, et al., J. Am. Chem. Soc. 135(2013) 2124-2127. doi: 10.1021/ja312277g
92. [92]
  J.M. Antos, M.B. Francis, J. Am. Chem. Soc. 126(2004) 10256-10257. doi: 10.1021/ja047272c
93. [93]
  J.M. Antos, J.M. McFarland, A.T. Iavarone, et al., J. Am. Chem. Soc. 131(2009) 6301-6308. doi: 10.1021/ja900094h
94. [94]
  B.V. Popp, Z.T. Ball, J. Am. Chem. Soc. 132(2010) 6660-6662. doi: 10.1021/ja101456c
95. [95]
  J. Xie, Z.Z. Huang, Angew. Chem. Int. Ed. 49(2010) 10181-10185. doi: 10.1002/anie.201004940
96. [96]
  L. Zhao, C.J. Li, Angew. Chem. Int. Ed. 47(2008) 7075-7078. doi: 10.1002/anie.v47:37
97. [97]
  K. Li, Q. Wu, J. Lan, et al., Nat. Commun. 6(2015) 8404. doi: 10.1038/ncomms9404
98. [98]
  G. Zhang, Y. Zhang, R. Wang, Angew. Chem. Int. Ed. 50(2011) 10429-10432. doi: 10.1002/anie.201105123
99. [99]
  S. Datta, A. Bayer, U. Kazmaier, Org. Biomol. Chem. 10(2012) 8268-8275. doi: 10.1039/c2ob26351c
100. [100]
  A. Bayer, U. Kazmaier, J. Org. Chem. 79(2014) 8491-8497. doi: 10.1021/jo501731y
101. [101]
  J. Gui, Q. Zhou, C.M. Pan, et al., J. Am. Chem. Soc. 136(2014) 4853-4856. doi: 10.1021/ja5007838
102. [102]
  M. Meldal, C.W. Tornøe, Chem. Rev. 108(2008) 2952-3015. doi: 10.1021/cr0783479
103. [103]
  J.F. Lutz, Angew. Chem. Int. Ed. 46(2007) 1018-1025. doi: 10.1002/(ISSN)1521-3773
104. [104]
  J.P. Brand, J. Charpentier, J. Waser, Angew. Chem. Int. Ed. 48(2009) 9346-9349. doi: 10.1002/anie.v48:49
105. [105]
  G.L. Tolnai, J.P. Brand, J. Waser, Beilstein J. Org. Chem. 12(2016) 745-749. doi: 10.3762/bjoc.12.74
106. [106]
  M.B. Hansen, F. Hubálek, T. Skrydstrup, et al., Chem. Eur. J. 22(2016) 1572-1576. doi: 10.1002/chem.201504462
107. [107]
  Z. Ruan, N. Sauermann, E. Manoni, et al., Angew. Chem. Int. Ed. 56(2017) 3172-3176. doi: 10.1002/anie.201611118
108. [108]
  L. Li, S. Ding, Y. Yang, et al., Chem. Eur. J. 23(2017) 1166-1172. doi: 10.1002/chem.201605034
109. [109]
  T. Willemse, W. Schepens, H. Vlijmen, et al., Catalysts 7(2017) 74. doi: 10.3390/catal7030074
110. [110]
  M. Kaiser, C. Siciliano, I. Assfalg-Machleidt, et al., Org. Lett. 5(2003) 3435-3437. doi: 10.1021/ol035178f
111. [111]
  O. Skaff, K.A. Jolliffe, C.A. Hutton, J. Org. Chem. 70(2005) 7353-7363. doi: 10.1021/jo051076m
112. [112]
  X. Lu, Y. Wang, B. Zhang, et al., J. Am. Chem. Soc. 139(2017) 12632-12637. doi: 10.1021/jacs.7b06469
113. [113]
  X. Lu, J. Yi, Z.Q. Zhang, et al., Chem. Eur. J. 20(2014) 15339-15343. doi: 10.1002/chem.v20.47
114. [114]
  J. Xu, E.A. Ahmed, B. Xiao, et al., Angew. Chem. Int. Ed. 54(2015) 8231-8235. doi: 10.1002/anie.201502308
115. [115]
  M.E. Phelps, Proc. Nat. Acad. Sci. 97(2000) 9226-9233. doi: 10.1073/pnas.97.16.9226
116. [116]
  P.W. Miller, N.J. Long, R. Vilar, et al., Angew. Chem. Int. Ed. 47(2008) 8998-9033. doi: 10.1002/anie.v47:47
117. [117]
  J.J. Dai, C. Fang, B. Xiao, et al., J. Am. Chem. Soc. 135(2013) 8436-8439. doi: 10.1021/ja404217t
118. [118]
  X. Huang, W. Liu, H. Ren, et al., J. Am. Chem. Soc. 136(2014) 6842-6845. doi: 10.1021/ja5039819
119. [119]
  D.D. Bume, C.R. Pitts, R.T. Jokhai, et al., Tetrahedron 72(2016) 6031-6036. doi: 10.1016/j.tet.2016.08.018
120. [120]
  R.Y. Zhu, K. Tanaka, G.C. Li, et al., J. Am. Chem. Soc. 137(2015) 7067-7070. doi: 10.1021/jacs.5b04088
121. [121]
  Q. Zhang, X.S. Yin, K. Chen, et al., J. Am. Chem. Soc. 137(2015) 8219-8226. doi: 10.1021/jacs.5b03989
122. [122]
  J. Miao, K. Yang, M. Kurek, et al., Org. Lett. 17(2015) 3738-3741. doi: 10.1021/acs.orglett.5b01710
123. [123]
  E.E. Gray, M.K. Nielsen, K.A. Choquette, et al., J. Am. Chem. Soc. 138(2016) 10802-10805. doi: 10.1021/jacs.6b06770
124. [124]
  S.A. Girard, T. Knauber, C.J. Li, Angew. Chem. Int. Ed. 53(2014) 74-100. doi: 10.1002/anie.v53.1
125. [125]
  Y. Wang, G.X. Li, G. Yang, et al., Chem. Sci. 7(2016) 2679-2683. doi: 10.1039/C5SC04169D
126. [126]
  B.V.S. Reddy, L.R. Reddy, E.J. Corey, Org. Lett. 8(2006) 3391-3394.
127. [127]
  P.E. Gormisky, M.C. White, J. Am. Chem. Soc. 135(2013) 14052-14055. doi: 10.1021/ja407388y
128. [128]
  T. Nanjo, E.C. de Lucca, M.C. White, J. Am. Chem. Soc.139(2017) 14586-14591. doi: 10.1021/jacs.7b07665
129. [129]
  T.J. Osberger, D.C. Rogness, J.T. Kohrt, et al., Nature 537(2016) 214-219. doi: 10.1038/nature18941
130. [130]
  X. Li, X. Che, G.H. Chen, et al., Org. Lett. 18(2016) 1234-1237. doi: 10.1021/acs.orglett.5b03690
131. [131]
  R. Curci, L. D'Accolti, C. Fusco, Acc. Chem. Res. 39(2006) 1-9. doi: 10.1021/ar050163y
132. [132]
  C. Annese, L. D'Accolti, M. De Zotti, et al., J. Org. Chem. 75(2010) 4812-4816. doi: 10.1021/jo100855h
133. [133]
  M.R. Rella, P.G. Williard, J. Org. Chem. 72(2007) 525-531. doi: 10.1021/jo061910n
134. [134]
  R. Saladino, M. Mezzetti, E. Mincione, et al., J. Org. Chem. 64(1999) 8468-8474. doi: 10.1021/jo990185w
135. [135]
  C. Annese, I. Fanizza, C.D. Calvano, et al., Org. Lett. 13(2011) 5096-5099. doi: 10.1021/ol201971v
136. [136]
  G. He, Y. Zhao, S. Zhang, et al., J. Am. Chem. Soc. 134(2012) 3-6. doi: 10.1021/ja210660g
137. [137]
  G. He, S.Y. Zhang, W.A. Nack, et al., Angew. Chem. Int. Ed. 52(2013) 11124-11128. doi: 10.1002/anie.201305615
138. [138]
  Q. Zhang, K. Chen, W. Rao, et al., Angew. Chem. Int. Ed. 52(2013) 13588-13592. doi: 10.1002/anie.201306625
139. [139]
  M. Yang, X. Jiang, Z.J. Shi, Org. Chem. Front. 2(2015) 51-54. doi: 10.1039/C4QO00282B
140. [140]
  E. Hernando, J. Villalva, A. Manu Martinez, et al., ACS Catal. 6(2016) 6868-6882. doi: 10.1021/acscatal.6b01987
141. [141]
  A. Sharma, J.F. Hartwig, Nature 517(2015) 600-604. doi: 10.1038/nature14127
142. [142]
  R.R. Karimov, A. Sharma, J.F. Hartwig, ACS Central Sci. 2(2016) 715-724. doi: 10.1021/acscentsci.6b00214
143. [143]
  X. Huang, T.M. Bergsten, J.T. Groves, J. Am. Chem. Soc.137(2015) 5300-5303. doi: 10.1021/jacs.5b01983
144. [144]
  A. Suzuki, Angew. Chem. Int. Ed. 50(2011) 6722-6737. doi: 10.1002/anie.201101379
145. [145]
  C.T. Yang, Z.Q. Zhang, Y.C. Liu, et al., Angew. Chem. Int. Ed. 50(2011) 3904-3907. doi: 10.1002/anie.201008007
146. [146]
  C.T. Yang, Z.Q. Zhang, H. Tajuddin, et al., Angew. Chem. Int. Ed. 51(2012) 528-532. doi: 10.1002/anie.201106299
147. [147]
  J. Yi, J.H. Liu, J. Liang, et al., Adv. Synth. Catal. 354(2012) 1685-1691. doi: 10.1002/adsc.201200136
148. [148]
  L. Li, T. Gong, X. Lu, et al., Nat. Commun. 8(2017) 345. doi: 10.1038/s41467-017-00363-4
149. [149]
  W. Su, T.J. Gong, X. Lu, et al., Angew. Chem. Int. Ed. 54(2015) 12957-12961. doi: 10.1002/anie.v54.44
150. [150]
  W. Su, T.J. Gong, Q. Zhang, et al., ACS Catal. 6(2016) 6417-6421. doi: 10.1021/acscatal.6b02039
151. [151]
  D.B. Diaz, A.K. Yudin, Nat. Chem. 9(2017) 731-742. doi: 10.1038/nchem.2814
152. [152]
  T. Ishiyama, J. Takagi, J.F. Hartwig, et al., Angew. Chem. Int. Ed. 41(2002) 3056-3058. doi: 10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-#
153. [153]
  J.Y. Cho, M.K. Tse, D. Holmes, et al., Science 295(2002) 305-308. doi: 10.1126/science.1067074
154. [154]
  F.M. Meyer, S. Liras, A. Guzman-Perez, et al., Org. Lett. 12(2010) 3870-3873. doi: 10.1021/ol1015674
155. [155]
  H. Audi, E. Rémond, M.J. Eymin, et al., Eur. J. Org. Chem. (2013) (2013) 7960-7972.
156. [156]
  V.A. Kallepalli, F. Shi, S. Paul, et al., J. Org. Chem. 74(2009) 9199-9201. doi: 10.1021/jo901822b
157. [157]
  P.G.M. Wuts, L.J. Simons, B.P. Metzger, et al., ACS Med. Chem. Lett. 6(2015) 645-649. doi: 10.1021/acsmedchemlett.5b00029
158. [158]
  L.S. Zhang, G. Chen, X. Wang, et al., Angew. Chem. Int. Ed. 53(2014) 3899-3903. doi: 10.1002/anie.201310000
159. [159]
  Y. Yang, C. Wang, Sci. China Chem. 58(2015) 1266-1279. doi: 10.1007/s11426-015-5375-0
160. [160]
  Y.J. Liu, Y.H. Liu, Z.Z. Zhang, et al., Angew. Chem. Int. Ed. 55(2016) 13859-13862. doi: 10.1002/anie.201607766
161. [161]
  J.N. deGruyter, L.R. Malins, P.S. Baran, Biochemistry 56(2017) 3863-3873. doi: 10.1021/acs.biochem.7b00536
162. [162]
  S. Sengupta, G. Mehta, Tetrahedron Lett. 58(2017) 1357-1372. doi: 10.1016/j.tetlet.2017.02.069
163. [163]
  E.V. Vinogradova, C. Zhang, A.M. Spokoyny, et al., Nature 526(2015) 687-691. doi: 10.1038/nature15739
164. [164]
  H.G. Lee, G. Lautrette, B.L. Pentelute, et al., Angew. Chem. Int. Ed. 56(2017) 3177-3181. doi: 10.1002/anie.201611202
165. [165]
  L.R. Malins, Pept. Sci. (2018), doi:http://dx.doi.org/10.1002/pep1002.24049. doi: 10.1002/pep1002.24049
166. [166]
  S. Bloom, C. Liu, D.K. Kolmel, et al., Nat. Chem. 10(2018) 205-211.
167. [167]
  S.J. McCarver, J.X. Qiao, J. Carpenter, et al., Angew. Chem. Int. Ed. 56(2017) 728-732. doi: 10.1002/anie.201608207
168. [168]
  C. Li, J. Wang, L.M. Barton, et al., Science 356(2017) eaam7355. doi: 10.1126/science.aam7355
169. [169]
  T. Qin, J. Cornella, C. Li, et al., Science 352(2016) 801-805. doi: 10.1126/science.aaf6123
170. [170]
  W.M. Cheng, R. Shang, Y. Fu, ACS Catal. 7(2016) 907-911.
171. [171]
  X. Lu, B. Xiao, L. Liu, et al., Chem. Eur. J. 22(2016) 11161-11164. doi: 10.1002/chem.201602486
172. [172]
  Y. Jin, M. Jiang, H. Wang, et al., Sci. Rep. 6(2016) 20068. doi: 10.1038/srep20068
173. [173]
  H.J.C. Deboves, C.A.G.N. Montalbetti, R.F.W. Jackson, J. Chem. Soc. Perkin Trans. 1(2001) 1876-1884.
174. [174]
  X. Lu, B. Xiao, Z. Zhang, et al., Nat. Commun. 7(2016) 11129. doi: 10.1038/ncomms11129
175. [175]
  K.M.M. Huihui, J.A. Caputo, Z. Melchor, et al., J. Am. Chem. Soc. 138(2016) 5016-5019. doi: 10.1021/jacs.6b01533
176. [176]
  X. Wang, Y. Dai, H. Gong, Top. Curr. Chem. 374(2016) 43. doi: 10.1007/s41061-016-0042-2
177. [177]
  J.S. Zheng, S. Tang, Y.K. Qi, et al., Nat. Protoc. 8(2013) 2483-2495. doi: 10.1038/nprot.2013.152
178. [178]
  Y.M. Li, Y.T. Li, M. Pan, et al., Angew. Chem. Int. Ed. 53(2014) 2198-2202. doi: 10.1002/anie.201310010
179. [179]
  J.S. Zheng, M. Yu, Y.K. Qi, et al., J. Am. Chem. Soc. 136(2014) 3695-3704. doi: 10.1021/ja500222u
180. [180]
  S. Tang, Y.Y. Si, Z.P. Wang, et al., Angew. Chem. Int. Ed. 54(2015) 5713-5717. doi: 10.1002/anie.201500051
181. [181]
  J. He, M. Wasa, K.S.L. Chan, et al., Chem. Rev. 117(2017) 8754-8786. doi: 10.1021/acs.chemrev.6b00622
182. [182]
  J.R. Chen, D.M. Yan, Q. Wei, et al., ChemPhotoChem 1(2017) 148-158. doi: 10.1002/cptc.201700008
183. [183]
  J. Twilton, C. Le, P. Zhang, et al., Nat. Rev. Chem. 1(2017) 0052. doi: 10.1038/s41570-017-0052
184. [184]
  J.R. Chen, X.Q. Hu, L.Q. Lu, et al., Acc. Chem. Res. 49(2016) 1911-1923. doi: 10.1021/acs.accounts.6b00254
185. [185]
  M.N. Hopkinson, A. Tlahuext-Aca, F. Glorius, Acc. Chem. Res. 49(2016) 2261-2272. doi: 10.1021/acs.accounts.6b00351
186. [186]
  J.C. Tellis, C.B. Kelly, D.N. Primer, et al., Acc. Chem. Res. 49(2016) 1429-1439. doi: 10.1021/acs.accounts.6b00214
187. [187]
  J. Zhang, Y. Chen, Acta Chim. Sinica 75(2017) 41-48. doi: 10.6023/A16080416
188. [188]
  Z. Feng, T. Zeng, J. Xuan, et al., Sci. China Chem. 59(2016) 171-174. doi: 10.1007/s11426-015-5548-x
189. [189]
  E.J. Horn, B.R. Rosen, Y. Chen, et al., Nature 533(2016) 77-81. doi: 10.1038/nature17431
190. [190]
  M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117(2017) 13230-13319. doi: 10.1021/acs.chemrev.7b00397
191. [191]
  S. Tang, Y. Liu, A. Lei, Chem. 4(2018) 27-45. doi: 10.1016/j.chempr.2017.10.001
192. [192]
  Z.W. Hou, Z.Y. Mao, Y.Y. Melcamu, et al., Angew. Chem. Int. Ed. 57(2018) 1636-1639. doi: 10.1002/anie.v57.6
193. [193]
  M. Movsisyan, E.I.P. Delbeke, J.K.E.T. Berton, et al., Chem. Soc. Rev. 45(2016) 4892-4928. doi: 10.1039/C5CS00902B
194. [194]
  D. Cambié, C. Bottecchia, N.J.W. Straathof, et al., Chem. Rev. 116(2016) 10276-10341. doi: 10.1021/acs.chemrev.5b00707
195. [195]
  B. Gutmann, D. Cantillo, C.O. Kappe, Angew. Chem. Int. Ed. 54(2015) 6688-6728. doi: 10.1002/anie.201409318
196. [196]
  J. Li, S.G. Ballmer, E.P. Gillis, et al., Science 347(2015) 1221-1226. doi: 10.1126/science.aaa5414
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