Record number :
Title of article :
α,β-Unsaturated acyl cyanide synthesis via triethylamine catalyzed redox cyanation
Author/Authors :
Choi، نويسنده , , Hyung Ho and Son، نويسنده , , Young Hoon and Jung، نويسنده , , Min Seok and Kang، نويسنده , , Eun Joo، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2011
Pages :
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Abstract :
Stereoselective redox cyanation of alkynyl aldehydes was explored, furnishing (E)-α,β-unsaturated acyl cyanides. This reaction was catalyzed by mild TEA base, as a dual role of Lewis base and Brönsted base. TMSCN treated with TEA was an effective reagent for generating umpolung intermediates from alkynyl aldehydes, and this nucleophilic intermediate can be protonated by equimolar amount of EtOH, promoting the efficient conversion into α,β-unsaturated acyl cyanides. The synthesized acyl cyanides were successfully applied as the synthetic precursors in the iron-catalyzed arylation reactions.
Keywords :
redox reaction , umpolung , acyl cyanide , Triethylamine
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters
Serial Year :
Link To Document :