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AlCl3 Catalyzed Coupling of N-benzylic Sulfonamides with 2-Substituted Cyanoacetates through Carbon-Nitrogen Bond Cleavage

Abstract

A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of the AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.

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Publication details

The article was received on 27 Apr 2017, accepted on 18 May 2017 and first published on 18 May 2017


Article type: Paper
DOI: 10.1039/C7OB01025G
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
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    AlCl3 Catalyzed Coupling of N-benzylic Sulfonamides with 2-Substituted Cyanoacetates through Carbon-Nitrogen Bond Cleavage

    C. Hu, G. Hong, X. Qian, K. R. Kim, X. Zhu and L. Wang, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB01025G

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