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Catalytic Regioselective Synthesis of Structurally Diverse Indene Derivatives from N-Benzylic Sulfonamides and Disubstituted Alkynes

Cong-Rong Liu, Fu-Lai Yang, Yi-Zhou Jin, Xian-Tao Ma, Dao-Juan Cheng, Nan Li and Shi-Kai Tian*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email: tianskustc.edu.cn

C.-R. Liu, F.-L. Yang, Y.-Z. Jin, X.-T. Ma, D.-J. Cheng, N. Li, S.-K. Tian, Org. Lett., 2010, 12, 3832-3835.

DOI: 10.1021/ol101524w


Abstract

In the presence of a catalytic amount of FeCl3, a broad range of N-benzylic sulfonamides smoothly react with internal alkynes to afford various functionalized indene derivatives with extremely high regioselectivity through FeCl3-catalyzed cleavage of sp3 carbon-nitrogen bonds to generate benzyl cation intermediates.

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Key Words

Indenes


ID: J54-Y2010-2470