Citation: Wu Zhengxing, Zhang Wanbin. Recent Advances in Metal-Catalyzed 1, 2-Difunctionalization of Conjugated Dienes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2250-2262. doi: 10.6023/cjoc201704031 shu

Recent Advances in Metal-Catalyzed 1, 2-Difunctionalization of Conjugated Dienes

Wu Zhengxing ,
Zhang Wanbin ^,

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Corresponding author: Zhang Wanbin, wanbin@sjtu.edu.cn
Received Date: 18 April 2017
Revised Date: 22 May 2017
Available Online: 24 September 2017
Fund Project: the Program of Shanghai Subject Chief Scientists 14XD1402300the National Natural Science Foundation of China 21232004the National Natural Science Foundation of China 21672142the Basic Research Foundation of Shanghai Science and Technology Committee 15JC1402200Project supported by the National Natural Science Foundation of China (Nos. 21232004, 21672142), the Program of Shanghai Subject Chief Scientists (No.14XD1402300) and the Basic Research Foundation of Shanghai Science and Technology Committee (No. 15JC1402200)

Figures(9)

The 1, 2-difunctionalization of conjugated dienes is an important homogeneous catalytic reaction. The obtained products through 1, 2-difunctionalization are widely existed in natural products and bioactive compounds, and are also sources of important organic intermediates, in addition, the preserved double bond in the difunctionalized product can be further transformed to give the desired structures or be functionalized sequentially to achieve multi-functionalization. The main difficulties focus on the encountered complex selectivities, including the regioselectivity, chemoselectivity and stereoselectivity in reactions. In recent years, with the development of organometallic chemistry, metal palladium, copper, iron or silver catalyzed 1, 2-difunctionalizations of conjugated dienes have been reported in succession. In some cases the enantioselective 1, 2-difunctionalizations of conjugated dienes were achieved via the introduction of chiral ligands. This review mainly focus on the recent metal catalyzed 1, 2-difunctionalizations of conjugated dienes.
- metal-catalyzed,
- conjugated diene,
- 1, 2-difunctionalization
1. [1]
2. [2]
3. [3]
  Prileschajew, N. Eur. J. Inorg. Chem. 1909, 42, 4811.
4. [4]
  Gilman, H. Organic Chemistry:An Advanced Treatise, Vol. 1, Wiley, New York, 1938, p. 36.
5. [5]
  (a) Criegee, R. Justus Liebigs Ann. Chem. 1936, 522, 75.
  (b) Criegee, R. Angew. Chem. 1937, 50, 153.
6. [6]
  Kwart, H.; Kahn, A. A. J. Am. Chem. Soc. 1967, 89, 1950. doi: 10.1021/ja00984a034
7. [7]
  (a) Sharpless, K. B.; Patrick, D. W.; Truesdale, L. K.; Biller, S. A. J. Am. Chem. Soc. 1975, 97, 2305.
  (b) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420.
8. [8]
  (a) Bäckvall, J.-E. Tetrahedron Lett. 1978, 19, 163.
  (b) Bäckvall, J.-E.; Björkman, E. E. J. Org. Chem. 1980, 45, 2893.
9. [9]
  (a) Sharpless, K. B.; Chong, A. O.; Oshima, K. J. Org. Chem. 1976, 41, 177.
  (b) Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263.
  (c) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
  (d) Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroeder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.
10. [10]
  (a) Aranyos, A.; Szabó, K. J.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 2523.
  (b) Itami, K.; Palmgren, A.; Thorarensen, A.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 6466.
  (c) Palmgren, A.; Larsson, A. L. E.; Bäckvall, J.-E. J. Org. Chem. 1999, 64, 836.
  (d) Löfstedt, J.; Närhi, K.; Dorange, I.; Bäckvall, J.-E. J. Org. Chem. 2003, 68, 7243.
  (e) Verboom, R. C.; Persson, B. A.; Bäckvall, J.-E. J. Org. Chem. 2004, 69, 3102.
  (f) Piera, J.; Persson, A.; Caldentey, X.; Bäckvall, J.-E. J. Am. Chem. Soc. 2007, 129, 14120.
  (g) Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134.
  (h) Schuster, C. H.; Li, B.; Morken, J. P. Angew. Chem. Int. Ed. 2011, 50, 7906.
11. [11]
  Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7571. doi: 10.1021/ja00045a044
12. [12]
  O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807. doi: 10.1021/jo00154a010
13. [13]
  (a) Larock, R. C.; Fried, C. A. J. Am. Chem. Soc. 1990, 112, 5882.
  (b) Larock, R. C.; Berrios-Pena, N. G.; Narayanan, K. J. Org. Chem. 1990, 55, 3447.
14. [14]
  (a) Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762.
  (b) Zhao, B.; Du, H.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 3523.
15. [15]
  Liao, L.; Jana, R.; Urkalan, K. B.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 5784. doi: 10.1021/ja201358b
16. [16]
  Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662. doi: 10.1021/jo00193a047
17. [17]
  Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308. doi: 10.1021/ja051181d
18. [18]
  Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066. doi: 10.1021/ja803397y
19. [19]
  Xing, D.; Yang, D. Org. Lett. 2013, 15, 4370. doi: 10.1021/ol401901h
20. [20]
  Cooper, S. P.; Booker-Milburn, K. I. Angew. Chem. Int. Ed. 2015, 54, 6496. doi: 10.1002/anie.201501037
21. [21]
  (a) Kagechika, K.; Shibasaki, M. J. Org. Chem. 1991, 56, 4093.
  (b) Kagechika, K.; Ohshima, T.; Shibasaki, M. Tetrahedron 1993, 49, 1773.
  (c) Ohshima, T.; Kagechika, K.; Adachi, A.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108.
22. [22]
  Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 11688. doi: 10.1021/ja074698t
23. [23]
  Cornwall, R. G.; Zhao, B.; Shi, Y. Org. Lett. 2013, 15, 796. doi: 10.1021/ol303469a
24. [24]
  Stokes, B. J.; Liao, L.; de Andrade, A. M.; Wang, Q.; Sigman, M. S. Org. Lett. 2014, 16, 4666. doi: 10.1021/ol502279u
25. [25]
  Wu, X.; Lin, H.-C.; Li, M.-L.; Li, L. L.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 13476. doi: 10.1021/jacs.5b08734
26. [26]
  Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314. doi: 10.1021/jacs.6b00976
27. [27]
  Chen, S.-S.; Meng, J.; Li, Y.-H.; Han, Z.-Y. J. Org. Chem., 2016, 81, 9402. doi: 10.1021/acs.joc.6b01611
28. [28]
  Chen, S.-S.; Wu, M.-S.; Han, Z.-Y. Angew. Chem., Int. Ed. 2017, 56, 6641. doi: 10.1002/anie.201702745
29. [29]
  Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589. doi: 10.1021/ol071105a
30. [30]
  Zhao, B.; Peng, X.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 11009. doi: 10.1021/ja103838d
31. [31]
  Zhao, B.; Peng, X.; Zhu, Y.; Ramirez, T. A.; Cornwall, R. G.; Shi, Y. J. Am. Chem. Soc. 2011, 133, 20890. doi: 10.1021/ja207691a
32. [32]
  Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 6610. doi: 10.1021/ja800495r
33. [33]
  Du, H.; Zhao, B.; Yuan, W.; Shi, Y. Org. Lett. 2008, 10, 4231. doi: 10.1021/ol801605w
34. [34]
  Zhao, B.; Du, H.; Shi, Y. J. Org. Chem. 2009, 74, 8392. doi: 10.1021/jo901685c
35. [35]
  Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 4570. doi: 10.1021/ja1013536
36. [36]
  Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370. doi: 10.1021/ja3046684
37. [37]
  (a) Llaveria, J.; Beltrán, Á.; Díaz-Requejo, M. M.; Matheu, M. I.; Castillón, S.; Pérez, P. J. Angew. Chem. Int. Ed. 2010, 49, 7092.
  (b) Llaveria, J.; Beltrán, Á.; Sameera, W. M. C.; Locati, A.; Díaz-Requejo, M. M.; Matheu, M. I.; Castillón, S.; Maseras, F.; Pérez, P. J. J. Am. Chem. Soc. 2014, 136, 5342.
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