Citation: Zhang Mingdi, Chen Bin, Ge Chen, Liu Renrong, Gao Jianrong, Jia Yixia. Nickel-Catalyzed Addition and Coupling Reaction of Aryl Triflates to Aldehydes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1636-1642. doi: 10.6023/cjoc201602007 shu

Nickel-Catalyzed Addition and Coupling Reaction of Aryl Triflates to Aldehydes

  • Corresponding author: Jia Yixia, yxjia@zjut.edu.cn
  • Received Date: 3 February 2016
    Revised Date: 9 March 2016

    Fund Project: the Program for New Century Excellent Talents in University No.NCET-12-1086the National Natural Science Foundation of China No. 21372202

Figures(1)

  • The nickel-catalyzed addition and coupling reaction between aryl triflates and aldehydes were developed. The reactions proceed smoothly in the presence of zinc powder with the use of 10 mol% Ni(dppe)Br2 as a catalyst. A range of aryl methanols and aryl ketones were isolated respectively in moderate to good yields in MeOH and THF solvent via direct addition or coupling reactions. Aliphatic and aromatic aldehydes were involved in this reaction, showing a broad substrate scope.
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    1. [1]

      Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (b) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644. (c) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048. (d) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533. (e) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349. 

    2. [2]

      Quan, L.-G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827. (b) Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2002, 67, 9428. (c) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. (d) Cacchi, S.; Fabrizi, G.; Gavazza, F.; Goggiamani, A. Org. Lett. 2003, 289. (e) Solé, D.; Serrano, O. Angew. Chem., Int. Ed. 2007, 46, 7270. (f) Solé, D.; Serrano, O. J. Org. Chem. 2008, 73, 9372. (g) Zhao, Y.-B.; Mariampillai, B.; Candito, D. A.; Laleu, B.; Li, M.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 1849. 

    3. [3]

      Majumdar, K. K.; Cheng, C.-H. Org. Lett. 2000, 2295. (b) Rayabarapu, D. K.; Chang, H.-T.; Cheng, C.-H. Chem. Eur. J. 2004, 10, 2991. (c) Hsieh, J. C.; Cheng, C.-H. Chem. Commun. 2005, 4554. (d) Hu, J.-X.; Wu, H.; Li, C.-Y.; Sheng, W.-J.; Jia, Y.-X.; Gao, J.-R. Chem. Eur. J. 2011, 17, 5234. (e) Yin, H.; Zhao, C.; You, H.; Lin, K.; Gong, H. Chem. Commun. 2012, 7034. (f) Wu, F.; Lu, W.; Qian, Q.; Ren, Q.; Gong, H. Org. Lett. 2012, 14, 3044. (g) He, J.-Q.; Chen, C.; Yu, W.-B.; Liu, R.-R.; Xu, M.; Li, Y.-J.; Gao, J.-R.; Jia, Y.-X. Tetrahedron Lett. 2014, 55, 2805. (h) Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 136, 17645.

    4. [4]

      Correa, A.; Martin, R. J. Am. Chem. Soc. 2014, 136, 7253. 

    5. [5]

      Huang, Y.-C.; Majumdar, K. K.; Cheng, C.-H. J. Org. Chem. 2002, 67, 1682.

    6. [6]

      Kuriyama, M.; Shimazawa, R.; Enomoto, T.; Shirai, R. J. Org. Chem. 2008, 73, 6939. (b) Infante, R.; Nieto, J.; Andrés, C. Org. Biomol. Chem. 2011, 9, 6691. (c) Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Onomura, O. Tetrahedron 2010, 66, 6814. (d) Yamamoto, T.; Ohta, T.; Ito, Y. Org. Lett. 2005, 7, 4153. (e) DeBerardinis, A. M.; Turlington, M.; Pu, L. Org. Lett. 2008, 10, 2709. (f) Yamamoto, T.; Furusawa, T.; Zhumagazin, A.; Yamakawa, T.; Oe, Y.; Ohta, T. Tetrahedron 2015, 71, 19. (g) Hirose, T.; Sugawara, K.; Kodama, K. J. Org. Chem. 2011, 76, 5413. (h) Majumdar, K. K.; Cheng, C.-H. Org. Lett. 2000, 2, 2295. 

    7. [7]

      Rao, M. L. N.; Venkatesh, V. Banerjee, D. Tetrahedron 2007, 63, 12917. (b) Silbestri, G. F.; Masson, R. B.; Lockhart, M. T.; Chopa, A. B. J. Organomet. Chem. 2006, 619, 1520. (c) Andrus, M. B.; Ma, Y.; Zang, Y.; Songa, C. Tetrahedron Lett. 2002, 43, 9137. (d) Ushijima, S.; Dohi, S.; Moriyama, K.; Togo, H. Tetrahedron 2012, 68, 1436. (e) Baghos, V. B.; Doss, S. H.; Eskander, E. F. Org. Prep. Proced. Int. 1993, 25, 301. (f) Meng, G.; Szostak, M. Org. Lett. 2015, 17, 4364. (g) Huang, Y. C.; Majumdar, K. K.; Cheng, C.-H. J. Org. Chem. 2002, 67, 1682. 

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