Chinese Journal of Catalysis

Chinese Journal of Catalysis ›› 2011, Vol. 32 ›› Issue (3): 472-476.DOI: 10.3724/SP.J.1088.2011.01018

• Research papers • Previous Articles     Next Articles

Cross-Coupling Reaction of Benzylic Halides with Allyltributylstannane Catalyzed by Cu(OTf)2

YU Xiaoqiang1, MA Yongjie1, ZHAO Ziran2,*, XU Zhanwei1, BAO Ming1,*   

  1. 1State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, Liaoning, China; 2Department of Plastic and Reconstructive Surgery, The First Hospital of Jilin University, Changchun 130021, Jilin, China
  • Received:2010-10-15 Revised:2010-12-08 Online:2011-03-04 Published:2014-08-01

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Abstract: Cross-coupling reaction of benzylic halides with allyltributylstannane was investigated. Desired cross-coupling products were obtained in satisfactory yields using Cu(OTf)2 as the catalyst. For example, cross-coupling product 1-(but-3-en-1-yl)-4-phenylnaphthalene (3b) was obtained in 93% yield when the reaction of 1-chloromethyl-4-phenylnaphthalene with allyltributylstannane was carried out in the presence of 10 mol% of Cu(OTf)2 in CH2Cl2 at room temperature for 1 h. The reaction of a substrate bearing an electron-donating group on the aromatic ring was completed in a few minutes, whereas the reaction of a substrate having an electron-withdrawing group on the aromatic ring needed prolonged reaction time. 3b, 1-bromo-4-(but-3-en-1-yl)naphthalene (3c), and 1-(but-3-en-1-yl)-4-nitronaphthalene (3f) were unknown compounds and their structure was confirmed by 1H NMR, 13C NMR, IR, and HRMS.

Key words: benzylic halide, allyltributylstannane, copper(II) trifluoromethanesulfonate, coupling reaction