title: Copper-catalyzed one-pot denitrogenative-dehydrogenative-decarboxylative coupling of β-ketoacids with trifluorodiazoethane: facile access to trifluoromethylated aldol products.
abstract: A novel copper-catalyzed one-pot cross-coupling of β-ketoacids with in situ generated trifluorodiazoethane has been developed. This reaction provides a direct and efficient method, in which one C-C bond and one C-O bond were formed in a carbenoid center with concomitant denitrogenation-dehydrogenation-decarboxylation, to afford trifluoromethylated aldol products. In several preliminary experiments, good to high enantioselectivities were also obtained.
authors.affiliation: Department of Chemistry, Key Laboratory of Systems Bioengineering (the Ministry of Education), Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072 (P. R. of China), Fax: (+86) 22-2740-3475.
authors.forename: Heng-Ying
authors.initials: HY
authors.lastname: Xiong
authors.forename: Zhen-Yan
authors.initials: ZY
authors.lastname: Yang
authors.forename: Zhen
authors.initials: Z
authors.lastname: Chen
authors.forename: Jun-Liang
authors.initials: JL
authors.lastname: Zeng
authors.forename: Jing
authors.initials: J
authors.lastname: Nie
authors.forename: Jun-An
authors.initials: JA
authors.lastname: Ma
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003653:Decarboxylation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D007651:Keto Acids / Q000737:chemistry*; D008745:Methylation; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: C000592527:2,2,2-trifluorodiazoethane; D000447:Aldehydes; D001391:Azo Compounds; D006845:Hydrocarbons, Fluorinated; D007651:Keto Acids; D003300:Copper; C116609:3-hydroxybutanal
keywords: 2,2,2-trifluorodiazoethane; decarboxylation; dehydrogenation cross-coupling reaction; enantioselectivity; β-ketoacids