title: Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers.
abstract: An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.
authors.affiliation: †School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
authors.forename: Hang
authors.initials: H
authors.lastname: Shen
authors.affiliation: †School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
authors.forename: Jiaqiang
authors.initials: J
authors.lastname: Li
authors.affiliation: †School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Liu
authors.affiliation: †School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Pan
authors.affiliation: †School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
authors.forename: Ruofeng
authors.initials: R
authors.lastname: Huang
authors.affiliation: †School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.|‡State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Xiong
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000604554:5-aminoisoxazole; C000604556:5-aminopyrazole; D000438:Alcohols; D004987:Ethers; D007555:Isoxazoles; D009570:Nitriles; D011720:Pyrazoles; D007455:Iodine