title: TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds.
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.
authors: Department of Science Education, Faculty of Education, Ibaraki University, Ibaraki 310-8512, Japan. satoru.matsukawa.1@vc.ibaraki.ac.jp.
authors: Satoru
authors: S
authors: Matsukawa
authors: Department of Science Education, Faculty of Education, Ibaraki University, Ibaraki 310-8512, Japan. varsil0403@gmail.com.
authors: Junya
authors: J
authors: Kimura
authors: Department of Science Education, Faculty of Education, Ibaraki University, Ibaraki 310-8512, Japan. 13p1419r@vc.ibaraki.ac.jp.
authors: Miki
authors: M
authors: Yoshioka
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis*
chemical_list: D000085:Acetates; D000447:Aldehydes; D053961:Azabicyclo Compounds; D002254:Carbonates; D007659:Ketones; D009570:Nitriles; C430593:cyanohydrin; C526482:triazabicyclodecene
keywords: basecatalyst; cyanation; cyanoester; guanidine; organocatalyst