Articles

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

  • Zhang Mingdi ,
  • Chen Bin ,
  • Ge Chen ,
  • Liu Renrong ,
  • Gao Jianrong ,
  • Jia Yixia
Expand
  • College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received date: 2016-02-03

  Revised date: 2016-03-09

  Online published: 2016-03-18

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372202) and the Program for New Century Excellent Talents in University (No. NCET-12-1086).

Abstract

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.

Cite this article

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

References

[1] (a) 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] (a) 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] (a) 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] Correa, A.; Martin, R. J. Am. Chem. Soc. 2014, 136, 7253.
[5] Huang, Y.-C.; Majumdar, K. K.; Cheng, C.-H. J. Org. Chem. 2002, 67, 1682.
[6] (a) 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] (a) 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.

Outlines

/