A novel copper (i) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides

David K. Johnson, Jeffrey P. Ciavarri, Faoud T. Ishmael, Kurl J. Schillinger, Thomas A.P. van Geel, Stephen M. Stratton

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Abstract

A comparative study of Li2CuCl4 vs Li2CuCl3 mediated mono-coupling reactions of dihalide substrates with allylmangnesium bromide is reported. Higher yields were obtained with Li2CuCl3 and the following trends in halide reactivity were observed Br > Cl for alkyl, aryl, and thiophenyl dihalides. and benzyl halide > phenyl halide. Utilizing these trends, a symmetrical coupling procedure for alkyl. aryl benzyl and thiophenyl dihalides, simply carried out by combining the dihalide with metallic magnesium and Li2CuCl4 is reported.

Original languageEnglish (US)
Pages (from-to)8565-8568
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number47
DOIs
Publication statusPublished - Nov 20 1995

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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