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Molecules 2016, 21(8), 1030; doi:10.3390/molecules21081030

TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds

Department of Science Education, Faculty of Education, Ibaraki University, Ibaraki 310-8512, Japan
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Academic Editor: Raquel P. Herrera
Received: 30 June 2016 / Revised: 27 July 2016 / Accepted: 3 August 2016 / Published: 10 August 2016
(This article belongs to the Collection Recent Advances in Organocatalysis)
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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. View Full-Text
Keywords: organocatalyst; basecatalyst; guanidine; cyanation; cyanoester organocatalyst; basecatalyst; guanidine; cyanation; cyanoester
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Matsukawa, S.; Kimura, J.; Yoshioka, M. TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds. Molecules 2016, 21, 1030.

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