Addition of chalcogenolate anions to terminal alkynes using microwave and solvent-free conditions: easy access to bis-organochalcogen alkenes
作者:Gelson Perin、Raquel G. Jacob、Luiz G. Dutra、Francisco de Azambuja、Greice F.F. dos Santos、Eder J. Lenardão
DOI:10.1016/j.tetlet.2005.11.158
日期:2006.2
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.