99967-30-3Relevant academic research and scientific papers
Lewis base catalyzed addition of trimethylsilyl cyanide to aldehydes
Denmark, Scott E.,Chung, Won-Jin
, p. 4002 - 4005 (2006)
A variety of achiral Lewis bases were found to catalyze the addition of TMSCN to the aldehydes. Among them, phosphines and amines were the most efficient catalysts. In addition, several chiral amines and phosphines were examined in a catalytic, asymmetric
α,β-Unsaturated acyl cyanide synthesis via triethylamine catalyzed redox cyanation
Choi, Hyung Ho,Son, Young Hoon,Jung, Min Seok,Kang, Eun Joo
scheme or table, p. 2312 - 2315 (2011/05/09)
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 Bro?nsted 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.
On the Preparation of Acyl Cyanides from Aldehydes
Haerle, Helmut,Jochims, Johannes C.
, p. 1400 - 1412 (2007/10/02)
The O-silylated cyanohydrins 3 prepared from the aldehydes 1 with trimethylsilyl cyanide are oxidized photochemically or thermally with N-bromosuccinimide to afford the acyl cyanides 4a-n.Scope and limitations of the procedure are discussed.
