Wiley-VCH Verlag, ChemInform, 20(37), 2006
Elsevier, Tetrahedron Letters, 6(47), p. 935-938
DOI: 10.1016/j.tetlet.2005.11.158
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We present here the reaction of diphenyl dichalcogenides (Se and Te) with propargyl alcohols using alumina supported sodium borohydride under solvent-free conditions. This efficient and improved method is general and furnishes the corresponding vinyl chalcogenide preferentially with a Z configuration. We also observed that when the same protocol was applied to phenyl acetylene, the (E)-bis-organochalcogen alkenes were obtained in good yields and high selectivity. The use of MW irradiation facilitates the procedure and accelerates the reaction. (c) 2005 Elsevier Ltd. All rights reserved.