Abstract
Cyanation reactions of carbonyl compounds with methyl cyanoformate or acetyl cyanide catalyzed by 5 mol % of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) were examined. Using methyl cyanoformate, the corresponding cyanohydrin carbonates were readily obtained in high yield for aromatic and aliphatic aldehydes and ketones. Similar results were obtained when acetyl cyanide was used as the cyanide source. The polymer-supported catalyst, PS-TBD, also acted as a good catalyst for this reaction. PS-TBD was easily recovered and reused with minimal activity loss.
Highlights
The addition of cyanide to carbonyl compounds is among the most fundamental carbon–carbon bond formation reactions in modern organic chemistry [1,2,3,4,5,6]
The resultant cyanohydrins are converted into important synthetic intermediates including α-hydroxyl-carbonyl compounds and β-amino alcohols
While hundreds of examples have been reported to this day, the inherent instability of trimethylsilyl cyanohydrins sometimes limits the applications of this reaction
Summary
The addition of cyanide to carbonyl compounds is among the most fundamental carbon–carbon bond formation reactions in modern organic chemistry [1,2,3,4,5,6]. To further extend the scope of this versatile synthetic reaction, we have examined the use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a Lewis base catalyst. It is well-known that TBD is a strong Lewis base owing to its distorted bicyclic guanidine structure [42,43]. N–H of group; TBD may actmethyl as a bifunctional effective foran theacidic cyanation carbonyl compounds using cyanoformate contains an acidic. Results and effective organobase catalystorfor the cyanation carbonyl compounds using methyl cyanoformate using methyl cyanoformate acetyl cyanide asof cyanide source.
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