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

doi:10.6023/cjoc201602007

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1636-1642.DOI: 10.6023/cjoc201602007 Previous Articles Next Articles

Articles

镍催化芳基三氟甲磺酸酯对醛的加成反应及偶联反应

张鸣頔, 陈斌, 葛晨, 刘人荣, 高建荣, 贾义霞

浙江工业大学化学工程学院杭州 310014

收稿日期:2016-02-03 修回日期:2016-03-09 发布日期:2016-03-18
通讯作者: 贾义霞 E-mail:yxjia@zjut.edu.cn
基金资助:
国家自然科学基金（No.21372202）和新世纪优秀人才支持计划（No.NCET-12-1086）资助项目.

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

Zhang Mingdi, Chen Bin, Ge Chen, Liu Renrong, Gao Jianrong, Jia Yixia

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2016-02-03 Revised:2016-03-09 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).

1. Nickel-Catalyzed Addition and Coupling Reaction of Aryl Triflates to Aldehydes.PDF(461KB)

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.

Key words: transition-metal catalysis, aryl triflate, addition reaction, coupling reaction

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]. Chin. J. Org. Chem., 2016, 36(7): 1636-1642.

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[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.

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镍催化芳基三氟甲磺酸酯对醛的加成反应及偶联反应

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

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