Citation: Zhang Zhenbei, Sun Wei, Cao Zhishan. Progress in Activation of Small Molecules Promoted by Frustrated Lewis Pairs[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1292-1318. doi: 10.6023/cjoc201801003 shu

Progress in Activation of Small Molecules Promoted by Frustrated Lewis Pairs

Zhang Zhenbei ^a,b,, ,
Sun Wei ^b ,
Cao Zhishan ^c

a.
College of Chemistry & Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453003
b.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
c.
College of Animal Science and Veterinary Medicine, Henan Institute of Science and Technology, Xinxiang 453003

Corresponding author: Zhang Zhenbei, zhenbei.zhang@hist.edu.cn
Received Date: 3 January 2018
Revised Date: 26 February 2018
Available Online: 8 June 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21473226)the National Natural Science Foundation of China 21473226

Figures(72)

Frustrated Lewis pairs (FLPs) chemistry has grown rapidly during the last decade and provided a new strategy for the activation of a variety of small molecules, such as hydrogen, olefins, alkynes, carbon dioxide, tetrahydrofuran and hydrosilane etc. The activations of these molecules have probided a new method in the utility of main group element. The structure and reactivity of FLPs are reviewed and the recent progress in activation of small molecules promoted by frustrated Lewis pairs is introduced.
- frustrated Lewis pairs,
- B (C₆F₅)₃,
- metal-free catalysis,
- organic synthesis
1. [1]
  Lewis, G. N. Valence and the Structure of Atoms and Molecules, Chemical Catalogue Company, New York, 1923.
2. [2]
  Shore, S. G.; Parry, R. W. J.Am.Chem. Soc. 1955, 77, 6084. doi: 10.1021/ja01627a103
3. [3]
  Brown, H. C.; Schlesinger, H. I.; Cardon, S. Z. J. Am.Chem.Soc. 1942, 64, 325. doi: 10.1021/ja01254a031
4. [4]
  (a) Wittig, G. ; Benz, E. Chem. Ber. 1959, 92, 1999.
  (b) Tochtermann, W. Angew. Chem., Int. Ed. Engl. 1966, 5, 351.
5. [5]
  (a) Bontemps, S. ; Bouhadir, G. ; Miqueu, K. ; Bourissou, D. J. Am. Chem. Soc. 2006, 128, 12056.
  (b) Grobe, J. ; Lütke-Brochtrup, K. ; Krebs, B. ; Läge, M. ; Niemeyer, H. -H. ; Würthwein E. -U. Z. Naturforsch. B 2006, 61, 882.
  (c) Hudnall, T. W. ; Kim, Y. M. ; Bebbington, M. W. P. ; Bourissou, D. ; Gabba, F. P. J. Am. Chem. Soc. 2008, 130, 10890.
  (d) Chiu, C. -B. ; Gabba, F. P. Dalton Trans. 2008, 814.
  (e) Lin, T. -P. ; Gualco, P. ; Ladeira, S. ; Amgoune, A. ; Bourissou, D. ; Gabba, F. P. C. R. Chim. 2010, 13, 1168.
  (f) Courtemanche, M. A. ; Legare, M. A. ; Maron, L. ; Fontaine, F. G. J. Am. Chem. Soc. 2013, 135, 9326
6. [6]
  Roesler, R.; Piers, W. E.; Parvez, M. J.Organomet. Chem. 2003, 680, 218. doi: 10.1016/S0022-328X(03)00384-X
7. [7]
  Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124. doi: 10.1126/science.1134230
8. [8]
  Welch, G. C.; Stephan, D. W. J.Am. Chem.Soc. 2007, 129, 1880. doi: 10.1021/ja067961j
9. [9]
  Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem.Commun. 2007, 5072.
10. [10]
  McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew.Chem., Int.Ed. 2007, 46, 4968. doi: 10.1002/(ISSN)1521-3773
11. [11]
  (a) Peng, B. ; Nie, Y. China Terminol. 2010, 12, 44(in Chinese).
  (彭斌, 聂永, 中国科技术语, 2010, 12, 44. )
  (b) Liu, Y. ; Du, H. Acta Chim. Sinica 2014, 72, 771(in Chinese).
  (刘勇兵, 杜海峰, 化学学报, 2014, 72, 711. )
12. [12]
  (a) Möming, C. M. ; Otten, E. ; Kehr, G. ; Frölich, R. ; Grimme, S. ; Stephan, D. W. ; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643.
  (b) Peuser, I. ; Neu, R. C. ; Zhao, X. ; Ulrich, M. ; Schirmer, B. ; Tannert, J. A. ; Kehr, G. ; Froehlich, R. ; Grimme, S. ; Erker, G. ; Stephan, D. W. Chem. -Eur. J. 2011, 17, 9640
13. [13]
  (a) Cardenas, A. J. P. ; Culotta, B. J. ; Warren, T. H. ; Grimme, S. ; Stute, A. ; Frölich, R. ; Kehr, G. ; Erker, G. Angew. Chem., Int. Ed. 2011, 50, 7567.
  (b) Neu, R. C. ; Otten, E. ; Lough, A. ; Stephan, D. W. Chem. Sci. 2011, 2, 170
14. [14]
  Sajid, M.; Klose, A.; Birkmann, B.; Liang, L.; Schirmer, B.; Wiegand, T.; Eckert, H.; Lough, A. J.; Fröhlich, R.; Daniliuc, C. G.; Grimme, S.; Stephan, D. W.; Kehr, G.; Erker, G. Chem.Sci. 2013, 4, 213. doi: 10.1039/C2SC21161K
15. [15]
  Möming, C. M.; Fröel, S.; Kehr, G.; Frölich, R.; Grimme, S.; Erker, G. J.Am.Chem.Soc. 2009, 131, 12280. doi: 10.1021/ja903511s
16. [16]
  Dureen, M. A.; Stephan, D. W. J.Am.Chem.Soc. 2009, 131, 8396. doi: 10.1021/ja903650w
17. [17]
  (a) Erker, G. ; Stephan, D. W. Frustrated Lewis Pairs I Uncovering and Understanding, Springer-Verlag, Berlin, Heidelberg, 2013.
  (b) Stephan, D. W. ; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46.
  (c) Stephan, D. W. ; Erker, G. Angew. Chem., Int. Ed. 2015, 54, 6400.
  (d) Lu, Z. ; Ye, H. ; Wang, H. Top. Curr. Chem. 2013, 334, 59.
  (e) Wang, H. ; Zheng, Y. ; Pan, Z. ; Fu, H. ; Ling, F. ; Zhong, W. Chin. J. Org. Chem. 2017, 37, 301(in Chinese).
  (王辉, 郑亿, 潘振涛, 傅鸿樑, 凌飞, 钟为慧, 有机化学, 2017, 37, 301. )
  (f) Stephan, D. W. Acc. Chem. Res. 2015, 48, 306.
  (g) Stephan, D. W. Org. Biomol. Chem. 2012, 10, 5740
18. [18]
  Schulz, F.; Sumerin, V.; Heikkinen, S.; Pedersen, B.; Wang, C.; Atsumi, M.; Leskel, M.; Repo, T.; Pyykkö, P.; Petry, W.; Rieger, B. J.Am. Chem.Soc. 2011, 133, 20245. doi: 10.1021/ja206394w
19. [19]
  Zaher, H.; Ashley, A. E.; Irwin, M.; Thompson, A. L.; Gutmann, M. J.; Krämera, T.; O'Hare D. Chem. Commun. 2013, 49, 9755. doi: 10.1039/c3cc45889j
20. [20]
  Karkamkar, A.; Parab, K.; Camaioni, D. M.; Neiner, D.; Cho, H. M.; Nielsen, T. K.; Autrey, T. Dalton Trans. 2013, 42, 615. doi: 10.1039/C2DT31628E
21. [21]
  Kim, H. W.; Rhee, Y. M. Chem.-Eur.J. 2009, 15, 13348. doi: 10.1002/chem.200902322
22. [22]
  Bakó, I.; Stirling, A.; Bálint, S.; Pápai, I. Dalton Trans. 2012, 41, 9023. doi: 10.1039/c2dt30370a
23. [23]
  Rocchigiani, L.; Ciancaleoni, G.; Zuccaccia, C.; Macchioni, A. J. Am.Chem.Soc. 2014, 136, 112. doi: 10.1021/ja4119169
24. [24]
  Marwitz, A. J. V.; Dutton, J. L.; Mercier, L. G.; Piers, W. E. J. Am.Chem.Soc. 2011, 133, 10026. doi: 10.1021/ja203214f
25. [25]
  Zhao, X.; Stephan, D. W. J.Am.Chem.Soc. 2011, 133, 12448. doi: 10.1021/ja205598k
26. [26]
  (a) Rokob, T. A. ; Hamza, A. ; Stirling, A. ; Soós, T. ; Pápai, I. Angew. Chem., Int. Ed. 2008, 47, 2435.
  (b) Grimme, S. ; Kruse, H. ; Goerigk, L. ; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 1402
27. [27]
  Schwendemann, S.; Fröhlich, R.; Kehr, G.; Erker, G. Chem.Sci. 2011, 2, 1842. doi: 10.1039/c1sc00124h
28. [28]
  (a) Axenov, K. ; Mömming, C. ; Kehr, G. ; Fröhlich, R. ; Erker, G. Chem. -Eur. J. 2010, 16, 14069.
  (b) Spies, P. ; Kehr, G. ; Bergander, K. ; Wibbeling, B. ; Fröhlich, R. ; Erker, G. Dalton Trans. 2009, 1534
29. [29]
  Wiegand, T.; Eckert, H.; Ekkert, O.; Fröhlich, R.; Kehr, G.; Erker, G.; Grimme, S. J.Am.Chem.Soc. 2012, 134, 4236. doi: 10.1021/ja210160k
30. [30]
  Wang, X.; Kehr, G.; Daniliuc, C. G.; Erker, G. J.Am.Chem. Soc. 2014, 136, 3293. doi: 10.1021/ja413060u
31. [31]
  (a) Rosorius, C. ; Daniliuc, C. G. ; Fröhlich, R. ; Kehr, G. ; Erker, G. J. Organomet. Chem. 2013, 744, 149.
  (b) Rosorius, C. ; Kehr, G. ; Fröhlich, R. ; Grimme, S., Erker, G. Organometallics 2011, 30, 4211
32. [32]
  (a) Stute, A. ; Kehr, G. ; Fröhlich, R. ; Erker, G. Chem. Commun. 2011, 47, 4288.
  (b) Stute, A. ; Kehr, G. ; Daniliuc, C. G. ; Fröhlich, R. ; Erker, G. Dalton Trans. 2013, 42, 4487
33. [33]
  Stute, A.; Heletta, L.; Fröhlich, R.; Daniliuc, C. G.; Kehr, G.; Erker, G. Chem.Commun. 2012, 48, 11739. doi: 10.1039/c2cc36782c
34. [34]
  Geier, S. J.; Stephan, D. W. J.Am.Chem.Soc. 2009, 131, 3476. doi: 10.1021/ja900572x
35. [35]
  Dureen, M. A.; Stephan, D. W. J.Am.Chem.Soc. 2010, 132, 13559. doi: 10.1021/ja1064153
36. [36]
  Xu, B.-H.; Bussmann, K.; Fröhlich, R.; Daniliuc, C. G.; Brandenburg, J. G.; Grimme, S.; Kehr, G.; Erker, G. Organometallics 2013, 32, 6745. doi: 10.1021/om4004225
37. [37]
  (a) Schwendemann, S. ; Oishi, S. ; Saito, S. ; Fröhlich, R. ; Kehr, G. ; Erker, G. Chem. -Asian J. 2013, 8, 212.
  (b) Lindqvist, M. ; Axenov, K. ; Nieger, M. ; Raeisaenen, M. ; Leskelä, M. ; Repo T. Chem. -Eur. J. 2013, 19, 10412
38. [38]
  Welch, G. C.; Masuda, J. D.; Stephan, D. W. Inorg.Chem. 2006, 45, 478. doi: 10.1021/ic051713r
39. [39]
  Wang, H., Fröhlich, R.; Kehr, G.; Erker, G. Chem.Commun. 2008, 5966.
40. [40]
  (a) Oezguen, T. ; Ye, K. -Y. ; Daniliuc, C. G. ; Wibbeling, B. ; Liu, L. ; Grimme, S. ; Kehr, G. ; Erker, G. Chem. -Eur. J. 2016, 22, 5988.
  (b) Oezguen, T. ; Bergander, K. ; Liu, L. ; Daniliuc, C. G. ; Grimme, S. ; Kehr, G. ; Erker, G. Chem. -Eur. J. 2016, 22, 11958
41. [41]
  Geier, S. J.; Gilbert, T. M.; Stephan, D. W. J.Am.Chem. Soc. 2008, 130, 12632. doi: 10.1021/ja805493y
42. [42]
  Blagg, R. J.; Lawrence, E. J.; Resner, K.; Oganesyan, V. S.; Herrington, T. J.; Ashley, A. E.; Wildgoose, G. G. Dalton Trans. 2016, 45, 6023. doi: 10.1039/C5DT01918D
43. [43]
  Ramos, A.; Lough, A. J.; Stephan, D. W. Chem.Commun. 2009, 1118.
44. [44]
  (a) Liptau, P. ; Neumann, M. ; Erker, G. ; Kehr, G. ; Fröhlich, R. ; Grimme, S. Organometallics 2004, 23, 21.
  (b) Huber, D. P. ; Kehr, G. ; Bergander, K. ; Fröhlich, R. ; Erker, G. ; Tanino, S. ; Ohki, Y. ; Tatsumi, K. Organometallics 2008, 27, 5279
45. [45]
  (a) Axenov, K. V. ; Kehr, G. ; Fröhlich, R. ; Erker, G. J. Am. Chem. Soc. 2009, 131, 3454.
  (b) Unverhau, K. ; Lübbe, G. ; Wibbeling, B. ; Fröhlich, R. ; Kehr, G. ; Erker, G. Organometallics 2010, 29, 5320
46. [46]
  (a) Ullrich, M. ; Lough, A. J. ; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 52.
  (b) Ullrich, M. ; Lough, A. J. ; Stephan, D. W. Organometallics 2010, 29, 3647
47. [47]
  Xing, J.-Y.; Buffet, J.-C.; Rees, N. H.; Norby, P.; O'Hare, D. Chem. Commun. 2016, 52, 10478. doi: 10.1039/C6CC04937K
48. [48]
  (a) Chase, P. A. ; Stephan, D. W. Angew. Chem., Int. Ed. 2008, 47, 7433.
  (b) Geier, S. J. ; Chase, P. A. ; Stephan, D. W. Chem. Commun. 2010, 46, 4884.
  (c) Holschumacher, D. ; Bannenberg, T. ; Hrib, C. G. ; Jones, P. G. ; Tamm, M. Angew. Chem., Int. Ed. 2008, 47, 7428
49. [49]
  Lam, J.; Guenther, B. A. R.; Farrell, J. M.; Eisenberger, P.; Bestvater, B. P.; Newman, P. D.; Melen, R. L.; Crudden, C. M.; Stephan, D. W. Dalton Trans. 2016, 45, 15303. doi: 10.1039/C6DT02202B
50. [50]
  Tao, X.; Kehr, G.; Wang, X.; Daniliuc, C. G.; Grimme, S.; Erker, G. Chem.-Eur. J. 2016, 22, 9504. doi: 10.1002/chem.201602058
51. [51]
  Chase, P. A.; Jurca, T., Stephan, D. W. Chem.Commun. 2008, 1701.
52. [52]
  (a) Tussing, S. ; Paradies, J. Dalton Trans. 2016, 45, 6124.
  (b) Tussing, S. ; Kaupmees, K. ; Paradies, J. Chem. -Eur. J. 2016, 22, 7422
53. [53]
  Courtemanche, M.-A.; Rochette, E.; Legare, M.-A.; Bi, W.; Fontaine, F.-G. Dalton Trans. 2016, 45, 6129. doi: 10.1039/C5DT03916A
54. [54]
  Sumerin, V.; Schulz, F.; Nieger, M.; Leskela, M.; Repo, T.; Rieger, B. Angew.Chem., Int.Ed. 2008, 47, 6001. doi: 10.1002/anie.200800935
55. [55]
  (a) Lu, Z. P. ; Cheng, Z. H. ; Chen, Z. X. ; Weng, L. H. ; Li, Z. H. ; Wang, H. D. Angew. Chem., Int. Ed. 2011, 50, 12227.
  (b) Yepes, D. ; Jaque, P. ; Fernandez, I. Chem. -Eur. J. 2016, 22, 18801
56. [56]
  Geier, S. J.; Gille, A. L.; Gilbert, T. M.; Stephan, D. W. Inorg. Chem. 2009, 48, 10466. doi: 10.1021/ic901726b
57. [57]
  Zheng, J.; Lin, Y.-J.; Wang, H. Dalton Trans. 2016, 45, 6088. doi: 10.1039/C5DT03815D
58. [58]
  (a) Liu, Y. ; Du, H. J. Am. Chem. Soc. 2013, 135, 6810.
  (b) Liu, Y. ; Du, H. J. Am. Chem. Soc. 2013, 135, 12968.
  (c) Wei, S. ; Du, H. J. Am. Chem. Soc. 2014, 136, 12261.
  (d) Wang, W. ; Meng, W. ; Du, H. Dalton Trans. 2016, 45, 5945.
  (e) Wang, W. ; Feng, X. ; Du, H. Org. Biomol. Chem. 2016, 14, 6683.
  (f) Ren, X. ; Du, H. J. Am. Chem. Soc. 2016, 138, 810.
  (g) Wang, Y. W. ; Chen, W. Q. ; Lu, Z. P. ; Li, Z. H. ; Wang, H. D. Angew. Chem., Int. Ed. 2013, 52, 7496
59. [59]
  (a) Stirling, A. ; Hamza, A. ; Rokob, T. A. ; Pápai, I. Chem. Commun. 2008, 3148.
  (b) Guo, Y. ; Li, S. Eur. J. Inorg. Chem. 2008, 2501
60. [60]
  Zhao, X.; Stephan, D. W. Chem.Sci. 2012, 3, 2123. doi: 10.1039/c2sc20262j
61. [61]
  Voss, T.; Mahdi, T.; Otten, E.; Fröhlich, R.; Kehr, G.; Stephan, D. W.; Erker, G. Organometallics 2012, 31, 2367. doi: 10.1021/om300017u
62. [62]
  Voss, T.; Chen, C.; Kehr, G.; Nauha, E.; Erker, G.; Stephan, D. W. Chem.-Eur. J. 2010, 16, 3005. doi: 10.1002/chem.v16:10
63. [63]
  Dornan, P. K.; Longobardi, L. E.; Stephan, D. W. Synlett 2014, 1521.
64. [64]
  Ullrich, M.; Seto, K. S.-H.; Lough, A. J.; Stephan, D. W. Chem. Commun. 2009, 2335.
65. [65]
  (a) Dureen, M. A. ; Brown, C. C. ; Stephan, D. W. Organometallics 2010, 29, 6594.
  (b) Ye, H. Y. ; Lu, Z. P. ; You, D. ; Chen, Z. X. ; Li, Z. H. ; Wang, H. D. Angew. Chem., Int. Ed. 2012, 51, 12047
66. [66]
  Yu, J.; Kehr, G.; Daniliuc, C. G.; Erker, G. Chem.Commun. 2016, 52, 1393. doi: 10.1039/C5CC07954C
67. [67]
  Fukazawa, A.; Yamada, H.; Yamaguchi, S. Angew.Chem., Int. Ed. 2008, 47, 5582. doi: 10.1002/anie.v47:30
68. [68]
  Klose, A.; Kehr, G.; Daniliuc, C. G.; Erker, G. Dalton Trans. 2016, 45, 2023. doi: 10.1039/C5DT03055B
69. [69]
  Tanur, C. A.; Stephan, D. W. Organometallics 2011, 30, 3652. doi: 10.1021/om200336t
70. [70]
  Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6422. doi: 10.1021/om1008346
71. [71]
  Zhao, X.; Lough, A.; Stephan, D. W. Chem.-Eur.J. 2011, 17, 6731. doi: 10.1002/chem.v17.24
72. [72]
  Zhao, X.; Gilbert, T. M.; Stephan, D. W. Chem.-Eur.J. 2010, 16, 10304. doi: 10.1002/chem.201001575
73. [73]
  Wilkins, L. C.; Gunther, B. A. R.; Walther, M.; Lawson, J. R.; Wirth, T.; Melen, R. L. Angew.Chem., Int.Ed. 2016, 55, 11292. doi: 10.1002/anie.201605239
74. [74]
  Mahdi, T.; Stephan, D. W. Angew.Chem., Int.Ed. 2013, 52, 12418. doi: 10.1002/anie.201307254
75. [75]
  Wittig, G.; Ruckert, A. Liebigs Ann.Chem. 1950, 566, 101. doi: 10.1002/(ISSN)1099-0690
76. [76]
  Breen, T. L.; Stephan, D. W. Inorg.Chem. 1992, 31, 4019. doi: 10.1021/ic00045a032
77. [77]
  (a) Avens, L. R. ; Barnhart, D. M. ; Burns, C. J. ; McKee, S. D. Inorg. Chem. 1996, 35, 537.
  (b) Campello, M. P. C. ; Domingos, A. ; Santos, I. J. Organomet. Chem. 1994, 484, 37
78. [78]
  Evans, W. J.; Leman, J. T.; Ziller, J. W.; Khan, S. I. Inorg. Chem. 1996, 35, 4283. doi: 10.1021/ic951627z
79. [79]
  Mommertz, A.; Leo, R.; Massa, W.; Harms, K.; Dehnicke, K. Z.Anorg. Allg.Chem. 1998, 624, 1647. doi: 10.1002/(ISSN)1521-3749
80. [80]
  (a) Breen, T. L. ; Stephan, D. W. Inorg. Chem. 1992, 31, 4019.
  (b) Guo, Z. Y. ; Bradley, P. K. ; Jordan, R. F. Organometallics 1992, 11, 2690.
  (c) Polamo, M. ; Mutikainen, I. ; Leskela, M. Acta Crystallogr. C 1997, 53, 1036
81. [81]
  GomezSaso, M.; Mullica, D. F.; Sappenfield, E.; Stone, F. G. A. Polyhedron 1996, 15, 793. doi: 10.1016/0277-5387(95)00328-7
82. [82]
  (a) Chivers, T. ; Schatte, G. Eur. J. Inorg. Chem. 2003, 3314.
  (b) Kunnari, S. M. ; Oilunkaniemi, R. ; Laitinen, R. S. ; Ahlgren, M. J. Chem. Soc., Dalton. Trans. 2001, 3417
83. [83]
  Campbell, J. P.; Gladfelter, W. L. Inorg.Chem. 1997, 36, 4094. doi: 10.1021/ic970171d
84. [84]
  Zhang, Z.; Miao, C.; Xia, C.; Sun, W. Org.Lett. 2016, 18, 1522. doi: 10.1021/acs.orglett.6b00157
85. [85]
  Birkmann, B.; Voss, T.; Geier, S. J.; Ullrich, M.; Kehr, G.; Erker, G.; Stephan, D. W. Organometallics 2010, 29, 5310. doi: 10.1021/om1003896
86. [86]
  Sgro, M. J.; Dömer, J.; Stephan, D. W. Chem.Commun. 2012, 48, 7253. doi: 10.1039/c2cc33301e
87. [87]
  Kreitner, C.; Geier, S. J.; Stanlake, L. J. E.; Caputo, C.; Stephan, D. W. Dalton Trans. 2011, 6771.
88. [88]
  Morton, J. G. M.; Dureen, M. A.; Stephan, D. W. Chem.Commun. 2010, 46, 8947. doi: 10.1039/c0cc02862b
89. [89]
  Neu, R. C.; Ménard, G.; Stephan, D. W. Dalton Trans. 2012, 41, 9016. doi: 10.1039/c2dt30206c
90. [90]
  Zhao, X.; Stephan, D. W. Chem.Commun. 2011, 47, 1833. doi: 10.1039/c0cc04791k
91. [91]
  Ashley, A. E.; Thompson, A. L.; OÏHare, D. Angew.Chem., Int.Ed. 2009, 48, 9839. doi: 10.1002/anie.v48:52
92. [92]
  Berkefeld, A.; Piers, W. E.; Parvez, M. J.Am.Chem. Soc. 2010, 132, 10660. doi: 10.1021/ja105320c
93. [93]
  Takeuchi, K.; Stephan, D. W. Chem.Commun. 2012, 48, 11304. doi: 10.1039/c2cc36470k
94. [94]
  Dobrovetsky, R.; Stephan, D. W. J.Am.Chem.Soc. 2013, 135, 4974. doi: 10.1021/ja401492s
95. [95]
  Zhang, Z.; Sun, Q.; Xia, C.; Sun, W. Org.Lett. 2016, 18, 6316. doi: 10.1021/acs.orglett.6b03030
96. [96]
  Liu, L.; Vankova, N.; Heine, T. Phys.Chem.Chem. Phys. 2016, 18, 3567. doi: 10.1039/C5CP06925D
97. [97]
  Ménard, G.; Stephan, D. W. J.Am.Chem.Soc. 2010. 132, 1796. doi: 10.1021/ja9104792
98. [98]
  Ménard, G.; Stephan, D. W. Angew.Chem., Int.Ed. 2011, 50, 8396. doi: 10.1002/anie.v50.36
99. [99]
  (a) Ghoussoub, M. ; Yadav, S. ; Ghuman, K. K. ; Ozin, G. A. ; Singh, C. V. ACS Catal. 2016, 6, 7109.
  (b) Ghuman, K. K. ; Hoch, L. B. ; Szymanski, P. ; Loh, J. Y. Y. ; Kherani, N. P. ; El-Sayed, M. A. ; Ozin, G. A. ; Singh, C. V. J. Am. Chem. Soc. 2016, 138, 1206.
  (c) Ghuman, K. K. ; Hoch, L. B. ; Wood, T. E. ; Mims, C. ; Singh, C. V. ; Ozin, G. A. ACS Catal. 2016, 6, 5764
100. [100]
  Sajid, M.; Kehr, G.; Daniliuc, C. G.; Erker, G. Angew.Chem., Int.Ed. 2014, 53, 1118. doi: 10.1002/anie.201307551
101. [101]
  Sajid, M.; Elmer, L. M.; Rosorius, C.; Daniliuc, C. G.; Grimme, S.; Kehr, G.; Erker, G. Angew.Chem., Int.Ed. 2013, 52, 2243. doi: 10.1002/anie.201208750
102. [102]
  Ye, K.-Y.; Kehr, G.; Daniliuc, C. G.; Liu, L.; Grimme, S.; Erker, G. Angew.Chem., Int.Ed. 2016, 55, 9216. doi: 10.1002/anie.201603760
103. [103]
  (a) Oestreich, M. ; Hermeke, J. ; Mohr, J. Chem. Soc. Rev. 2015, 44, 2202.
  (b) Fernandez-Alvarez, F. J. ; Aitani, A. M. ; Oro, L. A. Catal. Sci. Technol. 2014, 4, 611
104. [104]
  (a) Houghton, A. Y. ; Hurmalainen, J. ; Mansikkamaki, A. ; Piers, W. E. ; Tuononen, H. M. Nat. Chem. 2014, 6, 983.
  (b) Nikonov, G. I. ; Vyboishchikov, S. F. ; Shirobokov, O. G. J. Am. Chem. Soc. 2012, 134, 5488.
  (c) Mathew, J. ; Eguchi, K. ; Nakajima, Y. ; Sato, K. ; Shimada, S. ; Choe, Y. K. Eur. J. Org. Chem. 2017, 4922
105. [105]
  Parks, D. J.; Piers, W. E. J.Am.Chem.Soc. 1996, 118, 9440. doi: 10.1021/ja961536g
106. [106]
  (a) Parks, D. J. ; Blackwell, J. M. ; Piers, W. E. J. Org. Chem. 2000, 65, 3090.
  (b) Sakata, K. ; Fujimoto, H. J. Org. Chem. 2013, 78, 12505.
  (c) Keess, S. ; Simonneau, A. ; Oestreich, M. Organometallics 2015, 34, 790
107. [107]
  Blackwell, J. M.; Morrison, D. J.; Piers, W. E. Tetrahedron 2002, 58, 8247. doi: 10.1016/S0040-4020(02)00974-2
108. [108]
  Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org.Chem. 1999, 64, 4887. doi: 10.1021/jo9903003
109. [109]
  (a) Gevorgyan, V. ; Rubin, M. ; Liu, J. -X. ; Yamamoto, Y. J. Org. Chem. 2001, 66, 1672.
  (b) Bézier, D. ; Park, S. ; Brookhart, M. Org. Lett. 2013, 15, 496
110. [110]
  (a) Bajracharya, G. B. ; Nogami, T. ; Jin, T. ; Matsuda, K. ; Gevorgyan, V. ; Yamamoto, Y. Synthesis 2004, 308.
  (b) Nimmagadda, R. D. ; McRae, C. Tetrahedron Lett. 2006, 47, 5755.
  (c) Tan, M. ; Zhang, Y. Tetrahedron Lett. 2009, 50, 4912
111. [111]
  Porwal, D.; Oestreich, M. Synthesis 2017, 49, 4698. doi: 10.1055/s-0036-1588476
112. [112]
  Adduci, L. L.; McLaughlin, M. P.; Bender, T. A.; Becker, J. J.; Gagné, M. R. Angew.Chem., Int.Ed. 2014, 53, 1646. doi: 10.1002/anie.201306864
113. [113]
  Berkefeld, A.; Piers, W. E.; Parvez, M. J.Am.Chem. Soc. 2010, 132, 10660. doi: 10.1021/ja105320c
114. [114]
  Chen, J. W.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y. X. J.Am.Chem.Soc. 2016, 138, 5321. doi: 10.1021/jacs.6b01497
115. [115]
  (a) Harrison, D. J. ; McDonald, R. ; Rosenberg, L. Organometallics 2005, 24, 1398.
  (b) Lee, P. T. K. ; Skjel, M. K. ; Rosenberg, L. Organometallics 2013, 32, 1575.
  (c) Saito, K. ; Kondo, K. ; Akiyama, T. Org. Lett. 2015, 17, 3366-3369
116. [116]
  (a) Blackwell, J. M. ; Sonmor, E. R. ; Scoccitti, T. ; Piers, W. E. Org. Lett. 2000, 2, 3921.
  (b) Mewald, M. ; Oestreich, M. Chem. -Eur. J. 2012, 18, 14079.
  (c) Hermeke, J. ; Mewald, M. ; Oestreich, M. J. Am. Chem. Soc. 2013, 135, 17537
117. [117]
  (a) Rubin, M. ; Schwier, T. ; Gevorgyan, V. J. Org. Chem. 2002, 67, 1936.
  (b) Simonneau A. ; Oestreich, M. Angew. Chem., Int. Ed. 2013, 52, 11905.
  (c) Lee, P. T. K. ; Rosenberg, L. Dalton Trans. 2017, 46, 8818.
  (d) Zhang, L. W. ; Wen, Z. G. ; Borzov, M. ; Nie, W. L. Acta Chim. Sinica 2017, 75, 819(in Chinese).
  (张露文, 温志国, Borzov Maxim, 聂万丽, 化学学报, 2017, 75, 819. )
118. [118]
  (a) Gandhamsetty, N. ; Jeong, J. ; Park, J. ; Park, S. ; Chang, S. J. Org. Chem. 2015, 80, 7281.
  (b) Gandhamsetty, N. ; Park, J. ; Jeong, J. ; Park, S. W. ; Park, S. ; Chang, S. Angew. Chem., Int. Ed. 2015, 54, 6832
119. [119]
  Han, Y. X.; Zhang, S. T.; He, J. H.; Zhang, Y. T. J.Am. Chem.Soc. 2017, 139, 7399. doi: 10.1021/jacs.7b03534
120. [120]
  Curless, L. D.; Clark, E. R.; Dunsford, J. J.; Ingleson, M. J. Chem. Commun. 2014, 50, 5270. doi: 10.1039/C3CC47372D
121. [121]
  (a) Ma, Y. H. ; Wang, B. L. ; Zhang, L. ; Hou, Z. M. J. Am. Chem. Soc. 2016, 138, 3663.
  (b) Ma, Y. H. ; Zhang, L. ; Luo, Y. ; Nishiura, M. ; Hou, Z. M. J. Am. Chem. Soc. 2017, 139, 12434
122. [122]
  Otten, E.; Neu, R. C.; Stephan, D. W. J.Am.Chem. Soc. 2009, 131, 9918. doi: 10.1021/ja904377v
123. [123]
  Wang, T.; Kehr, G.; Liu, L.; Grimme, S.; Daniliuc, C. G.; Erker, G. J. Am.Chem.Soc. 2016, 138, 4302. doi: 10.1021/jacs.6b00325
124. [124]
  Dureen, M. A.; Welch, G. C.; Gilbert, T. M.; Stephan, D. W. Inorg. Chem. 2009, 48, 9910. doi: 10.1021/ic901590s
125. [125]
  Chase, P. A.; Gille, A. L.; Gilbert, T. M.; Stephan, D. W. Dalton Trans. 2009, 7179.
126. [126]
  Zhou, Q.; Zhang, L.; Meng, W.; Feng, X.; Yang, J.; Du, H. Org. Lett. 2016, 18, 5189. doi: 10.1021/acs.orglett.6b02610
127. [127]
  Li, S.; Li, G.; Meng, W.; Du, H. J.Am.Chem.Soc. 2016, 138, 12956. doi: 10.1021/jacs.6b07245
128. [128]
  Fan, X. T.; Zheng, J. H.; Li, Z. H.; Wang, H. D. J.Am. Chem.Soc. 2015, 137, 4916. doi: 10.1021/jacs.5b03147
129. [129]
  Zheng, J.; Fan, X.; Zhou, B.; Li, Z. H.; Wang, H. Chem.Commun. 2016, 52, 4655. doi: 10.1039/C6CC00347H
130. [130]
  Yu, Z.; Li, Y.; Shi, J.; Ma, B.; Liu, L.; Zhang, J. Angew.Chem., Int.Ed. 2016, 55, 14807. doi: 10.1002/anie.201608937
131. [131]
  Caputo, C. B.; Stephan, D. W. Organometallics 2012, 31, 27. doi: 10.1021/om200885c
132. [132]
  Froemel, S.; Daniliuc, C. G.; Bannwarth, C.; Grimme, S.; Bussmann, K.; Kehr, G.; Erker, G. Dalton Trans. 2016, 45, 19230. doi: 10.1039/C6DT04206F
133. [133]
  Samigullin, K.; Georg, I.; Bolte, M.; Lerner, H.-W.; Wagner, M. Chem.-Eur. J. 2016, 22, 3478. doi: 10.1002/chem.201504791
134. [134]
  Fasano, V.; Radcliffe, J. E.; Ingleson, M. J. ACS Catal. 2016, 6, 1793. doi: 10.1021/acscatal.5b02896
135. [135]
  Chernichenko, K.; Lindqvist, M.; Kotai, B.; Nieger, M.; Sorochkina, K.; Papai, I.; Repo, T. J.Am.Chem.Soc. 2016, 138, 4860. doi: 10.1021/jacs.6b00819
136. [136]
  Liu, Y. Z.; Fan, X. T.; Li, Z. H.; Wang, H. D. Chem.Commun. 2017, 53, 10890. doi: 10.1039/C7CC05028C
137. [137]
  Chen, G.-Q.; Kehr, G.; Daniliuc, C. G.; Erker, G. Dalton Trans. 2016, 45, 6820. doi: 10.1039/C6DT00857G
1. [1]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
2. [2]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
3. [3]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
4. [4]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
5. [5]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
6. [6]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
7. [7]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
8. [8]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
9. [9]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
10. [10]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
11. [11]
  Shasha Ma , Zujin Yang , Jianyong Zhang . Facile Synthesis of FeBTC Metal-Organic Gel and Its Adsorption of Cr₂O₇²⁻: A Physical Chemistry Innovation Experiment. University Chemistry, 2024, 39(8): 314-323. doi: 10.3866/PKU.DXHX202401008
12. [12]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
13. [13]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
14. [14]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
15. [15]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
16. [16]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
17. [17]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
18. [18]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
19. [19]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
20. [20]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

Get Citation

PDF

XML

Metrics

PDF Downloads(415)
Abstract views(13680)
HTML views(5884)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142