Citation: Zhong Zhuliang, Peng Xiao-Shui, Wong Henry N. C.. Recent advances on iron-catalyzed coupling reactions involving organolithium reagents[J]. Chinese Chemical Letters, ;2019, 30(8): 1463-1467. doi: 10.1016/j.cclet.2019.05.026 shu

Recent advances on iron-catalyzed coupling reactions involving organolithium reagents

Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Hong Kong, China

hncwong@cuhk.edu.hk

Received Date: 3 April 2019
Revised Date: 26 April 2019
Accepted Date: 30 April 2019
Available Online: 17 August 2019

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Owing to their inexpensive and environmentally friendly properties, iron-based catalysts have been actively investigated for new organic reactions. In this account, we summarized our recent results on iron-catalyzed cross-coupling reactions and homo-coupling reactions. With iron-based catalysts, we constructed diverse carbon-carbon bonds, i.e., C(sp²)-C(sp³), C(sp³)-C(sp³), C(sp³)-C(sp²) and C(sp²)-C(sp²) bonds. In order to demonstrate the usefulness of our iron protocol, we also carried out these reactions on gram-scale reactions, leading to good yields
- Iron-catalyzed,
- Cross-coupling,
- Homo-coupling,
- Organolithium,
- Gram-scale
1. [1]
  E.I. Negishi, Angew. Chem. Int. Ed. 50 (2011) 6738-6764. doi: 10.1002/anie.201101380
2. [2]
  M. Yamamura, I. Moritani, S.I. Murahashi, J. Organomet. Chem. 91 (1975) C39-C42. doi: 10.1016/S0022-328X(00)89636-9
3. [3]
  S. Murahashi, M. Yamamura, K. Yanagisawa, N. Mita, K. Kondo, J. Org. Chem. 44 (1979) 2408-2417. doi: 10.1021/jo01328a016
4. [4]
  M. Giannerini, M. Fañanás-Mastral, B.L. Feringa, Nat. Chem. 5 (2013) 667. doi: 10.1038/nchem.1678
5. [5]
  M. Giannerini, V. Hornillos, C. Vila, M. Fañanás-Mastral, B.L. Feringa, Angew. Chem. Int. Ed. 52 (2013) 13329-13333. doi: 10.1002/anie.201306427
6. [6]
  V. Hornillos, M. Giannerini, C. Vila, M. Fañanás-Mastral, B.L. Feringa, Org. Lett. 15 (2013) 5114-5117. doi: 10.1021/ol402408v
7. [7]
  C. Vila, M. Giannerini, V. Hornillos, M. Fañanás-Mastral, B.L. Feringa, Chem. Sci. 5 (2014) 1361-1367. doi: 10.1039/c3sc53047g
8. [8]
  C. Vila, V. Hornillos, M. Giannerini, M. Fañanás-Mastral, B.L. Feringa, Chem. -Eur. J. 20 (2014) 13078-13083. doi: 10.1002/chem.201404398
9. [9]
  L.M. Castelló, V. Hornillos, C. Vila, et al., Org. Lett. 17 (2015) 62-65. doi: 10.1021/ol5032409
10. [10]
  D. Heijnen, V. Hornillos, B.P. Corbet, M. Giannerini, B.L. Feringa, Org. Lett. 17 (2015) 2262-2265. doi: 10.1021/acs.orglett.5b00905
11. [11]
  E.B. Pinxterhuis, M. Giannerini, V. Hornillos, B.L. Feringa, Nat. Commun. 7 (2016) 11698. doi: 10.1038/ncomms11698
12. [12]
  D. Heijnen, F. Tosi, C. Vila, et al., Angew. Chem. Int. Ed. 56 (2017) 3354-3359. doi: 10.1002/anie.201700417
13. [13]
  C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 104 (2004) 6217-6254. doi: 10.1021/cr040664h
14. [14]
  Z. Jia, Q. Liu, X.S. Peng, H.N.C. Wong, Nat. Commun. 7 (2016) 10614. doi: 10.1038/ncomms10614
15. [15]
  X.L. Lu, M. Shannon, X.S. Peng, H.N.C. Wong, Org. Lett. 21 (2019) 2546-2549. doi: 10.1021/acs.orglett.9b00394
16. [16]
  Q. Liu, Z.Y. Wang, X.S. Peng, H.N.C. Wong, J. Org. Chem. 83 (2018) 6325-6333. doi: 10.1021/acs.joc.8b00510
17. [17]
  Z. Zhong, Z.Y. Wang, S.F. Ni, et al., Org. Lett. 21 (2019) 700-704. doi: 10.1021/acs.orglett.8b03893
18. [18]
  W.F. Bailey, T.V. Ovaska, J. Am. Chem. Soc. 115 (1993) 3080-3090. doi: 10.1021/ja00061a006
19. [19]
  J. Zhao, Z. Xu, K. Oniwa, et al., Angew. Chem. Int. Ed. 55 (2016) 259-263. doi: 10.1002/anie.201507794
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2. [2]
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