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α,β-Unsaturated acyl cyanide synthesis via triethylamine catalyzed redox cyanation

✍ Scribed by Hyung Ho Choi; Young Hoon Son; Min Seok Jung; Eun Joo Kang

Book ID: 104098976
Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 340 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2011.02.063

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✦ Synopsis

Stereoselective redox cyanation of alkynyl aldehydes was explored, furnishing (E)-a,b-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 a,b-unsaturated acyl cyanides. The synthesized acyl cyanides were successfully applied as the synthetic precursors in the iron-catalyzed arylation reactions.

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