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Synthesis 2009(23): 4015-4021  
DOI: 10.1055/s-0029-1217029
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cerium(III)-Mediated Efficient and Stereoselective Hydrochalcogenation of Terminal Alkynes

Claudio C. Silveira*, Samuel R. Mendes, Daniel D. Rosa, Gilson Zeni
Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil
Fax: +55(55)32208754; e-Mail: silveira@quimica.ufsm.br;
Further Information

Publication History

Received 15 May 2009
Publication Date:
12 October 2009 (online)

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Abstract

Vinylic chalcogenides were synthesized stereospecifically by hydrochalcogenation of propargylic amines or alcohols mediated by cerium(III) chloride. The products were obtained in good yields and with high regio- and stereoselectivities.

Key words

cerium chloride - vinylic chalcogenides - hydrochalcogenation - selenium - tellurium

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36

One equivalent of MeOH was used for the cleavage of diphenyl diselenide.