Citation: Xu Fangning, Han Wei. Research Progress in Transition-Metal-Free Carbonylation Reactions[J]. Chinese Journal of Organic Chemistry, ;2018, 38(10): 2519-2533. doi: 10.6023/cjoc201804017 shu

Research Progress in Transition-Metal-Free Carbonylation Reactions

Xu Fangning ^a ,
Han Wei ^,

School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023

Corresponding author: Han Wei, hanwei@njnu.edu.cn
Received Date: 10 April 2018
Revised Date: 28 May 2018
Available Online: 7 October 2018
Fund Project: the National Natural Science Foundation of China 21776139the Natural Science Foundation of Jiangsu Provincial Colleges and Universities 16KJB150019Project supported by the National Natural Science Foundation of China (No. 21776139), the Natural Science Foundation of Jiangsu Province (No. BK20161553), the Natural Science Foundation of Jiangsu Provincial Colleges and Universities (No. 16KJB150019), the Qing Lan Project of Nanjing Normal University and the Priority Academic Program Development of Jiangsu Higher Education Institutionsthe Natural Science Foundation of Jiangsu Province BK20161553

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Carbon monoxide is a readily available and cheap C1 feedstock. Carbonylation, the direct incorporation of carbon monoxide into organic molecules, is a very important and fundamental chemical transformation. In recent years, developing transition-metal-free systems for the carbonylation has attracted highly attention from many researchers. The recent rearch progress of transition-metal-free carbonylations for the synthesis of aldehydes, ketones, esters, amides, acids, anhydrides, acyl chloride, and alcohols is reviewed. And the development and application prospects for transition-metal-free carbonylation are also discussed.
- carbon monoxide,
- carbonylation,
- transition-metal-free,
- synthetic methods
1. [1]
  (a) Beller, M. Catalytic Carbonyladon Reactions, Springer-Verlag Berlin, Heidelberg, 2006.
  (b) Kollά, L. Modem Carbonylation Methods, Wiley-VCH, Weinheim, 2008.
  (c) Wu, X.-F.; Beller, M. Transition Metal Catalyzed Carbonylation Reactions-Carbonylative Activation of C-X Bonds, Springer-Verlag Berlin, Heidelberg, 2013.
2. [2]
  Hagen, J. Industrial Catalysis, Wiley-VCH, Weinheim, 2006.
3. [3]
  Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation:Direct Synthesis of Carbonyl Compounds, Plenum Press, New York, 1991.
4. [4]
5. [5]
  Ryu, I.; Kusano K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295. doi: 10.1021/ja00159a088
6. [6]
  Ryu, I.; Kusano, K.; Masumi, N.; Yamazaki, H.; Ogawa, A.; Sonoda N. Tetrahedron Lett. 1990, 31, 6887. doi: 10.1016/S0040-4039(00)97198-3
7. [7]
  Ryu, I.; Hasegawa, M.; Kurihara, A.; Ogawa, A.; Tsunoi, S.; Sonoda, N. Synlett 1993, 143.
8. [8]
  Ryu, I.; Uehara, S.; Hirao, H.; Fukuyama, T. Org. Lett. 2008, 10, 1005. doi: 10.1021/ol7031043
9. [9]
  Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. doi: 10.1021/ja962879h
10. [10]
  Uenoyama, Y.; Tsukida M.; Doi, T.; Ryu, I.; Studer, A. Org. lett. 2005, 7, 2985. doi: 10.1021/ol050951n
11. [11]
  Nishii, Y.; Nagano, T.; Gotoh, H.; Nagase, R.; Motoyoshiya, J.; Aoyama, H.; Tanabe, Y. Org. Lett. 2007, 9, 563. doi: 10.1021/ol062673d
12. [12]
  Jin, F.-L.; Han, W. Chem. Commun. 2015, 51, 9133. doi: 10.1039/C5CC01968K
13. [13]
  Jin, F.-L.; Zhong, Y.-Z.; Zhang, X.; Zhang, H.-C.; Zhao, Q.; Han, W. Green Chem. 2016, 18, 2598. doi: 10.1039/C6GC00017G
14. [14]
  Han, W.; Chen, J.-J.; Jin, F.-L.; Yuan, X.-R. Synlett 2018, 369.
15. [15]
  Gu, L.-J.; Jin, C.; Liu, J.-Y. Green Chem. 2015, 17, 3733. doi: 10.1039/C5GC00644A
16. [16]
  Zhang, H.-T.; Gu, L.-J.; Huang, X.-Z.; Wang, R.; Jin, C.; Li, G.-P. Chin. Chem. Lett. 2016, 27, 256. doi: 10.1016/j.cclet.2015.10.012
17. [17]
  Li, X.-G.; Liang, D.-Q.; Huang, W.-Z.; Zhou, H.-F.; Li, Z.; Wang, B.-L.; Ma, Y.-H.; Wang, H. Tetrahedron 2016, 72, 8442. doi: 10.1016/j.tet.2016.11.009
18. [18]
  Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. doi: 10.1021/ja964124g
19. [19]
  Kreimerman, S.; Ryu, I.; Minakata, S.; Komatsu, M. Org. Lett. 2000, 2, 389. doi: 10.1021/ol9913441
20. [20]
  Zhang, H.; Shi, R.-Y.; Ding, A.-X.; Lu, L.-J.; Chen, B.-R.; Lei, A.-W. Angew. Chem., Int. Ed. 2012, 51, 12542. doi: 10.1002/anie.201206518
21. [21]
  Fukuoka, S. Ind. Eng. Chem. Res. 2016, 55, 4830. doi: 10.1021/acs.iecr.6b00606
22. [22]
  Guo, W.; Lu, L.-Q.; Wang, Y.; Wang, Y.-N.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 2265. doi: 10.1002/anie.201408837
23. [23]
  Majek, M.; Wangelin, A. J. Angew. Chem., Int. Ed. 2015, 54, 2270. doi: 10.1002/anie.201408516
24. [24]
  Koziakov, D.; Wangelin, A. J. Org. Biomol. Chem. 2017, 15, 6715. doi: 10.1039/C7OB01572K
25. [25]
  Lu, L.-J.; Cheng, D.-Y.; Zhan, Y.-F.; Shi, R.-Y.; Chiang, C.-W.; Lei, A.-W. Chem. Commun. 2017, 53, 6852. doi: 10.1039/C7CC03671J
26. [26]
  Kim, S.; Kim, S.; Otsuka, N.; Ryu, I. Angew. Chem., Int. Ed. 2005, 44, 6183. doi: 10.1002/(ISSN)1521-3773
27. [27]
  Ryu, I.; Nagahara, K.; Kambe, N.; Sonoda, N.; Kreimerman, S.; Komatsu, M. Chem. Commun. 1998, 18, 1953.
28. [28]
  Kawamoto, T.; Sato, A.; Ryu, I. Chem.-Eur. J. 2015, 21, 14764. doi: 10.1002/chem.201503164
29. [29]
  Lin, M.-R.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892.
30. [30]
  Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. doi: 10.1021/jo9718556
31. [31]
  Kirillova, M. V.; Kirillov A. M.; Kuznetsov, M. L.; Silva, J. A. L.; Silva, J. J. R. F.; Pombeiro, A. J. L. Chem. Commun. 2009, 2353.
32. [32]
  Thaler, W. A. J. Am. Chem. Soc. 1966, 88, 4278. doi: 10.1021/ja00970a042
33. [33]
  Gupta, V.; Kahne, D. Tetrahedron Lett. 1993, 34, 591. doi: 10.1016/S0040-4039(00)61627-1
34. [34]
  Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1997, 38, 7883. doi: 10.1016/S0040-4039(97)10076-4
35. [35]
  Kobayashi, S.; Kawamoto, T.; Uehara, S.; Fukuyama, T.; Ryu, I. Org. Lett. 2010, 12, 1548. doi: 10.1021/ol1002847
36. [36]
  Kawamoto, T.; Matsubara, H.; Ryu, I. Chem. Lett. 2014, 43, 1140. doi: 10.1246/cl.140370
37. [37]
  Kawamoto, T.; Okada, T.; Curran, D. P.; Ryu, I. Org. Lett. 2013, 15, 2144. doi: 10.1021/ol4006294
38. [38]
  Kawamoto, T.; Fukuyama, T.; Ryu, I. J. Am. Chem. Soc. 2012, 134, 875. doi: 10.1021/ja210585n
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