title: General and efficient one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones from sugar terminal alkynes by Sonogashira/tetra-n- butylammonium permanganate oxidation.
abstract: A new approach for one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones has been achieved by the reaction of various sugar terminal alkynes with heterocyclic(aryl) iodides at room temperature. This one-pot protocol includes Sonogashira coupling and mild n-Bu4NMnO4 oxidation reaction. This method is mild, general and efficient. Fifty-six examples have been given and the sugar/heterocyclic(aryl) 1,2-diketones were obtained in 71-94% yields. The sugar terminal alkynes include 9 structurally different sugars in pyranose, furanose, and acyclic form which have various protecting groups, sensitive groups, and sterically bulky substituents. The heterocyclic(aryl) iodides include sterically bulky heterocyclic compounds and iodobenzenes with electron-donating, electron-neutral, and electron-withdrawing substituents.
authors.affiliation: The Key Lab of Chemical Biology and Organic Chemistry, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, China. Electronic address: zhangfy@zzu.edu.cn.
authors.forename: Fuyi
authors.initials: F
authors.lastname: Zhang
authors.affiliation: The Key Lab of Chemical Biology and Organic Chemistry, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, China.
authors.forename: Xiaopei
authors.initials: X
authors.lastname: Wu
authors.affiliation: The Key Lab of Chemical Biology and Organic Chemistry, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, China.
authors.forename: Liming
authors.initials: L
authors.lastname: Wang
authors.affiliation: The Key Lab of Chemical Biology and Organic Chemistry, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, China. Electronic address: liuh6@zzu.edu.cn.
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
authors.affiliation: The Key Lab of Chemical Biology and Organic Chemistry, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, China; College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China.
authors.forename: Yufen
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D055772:Green Chemistry Technology; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007462:Iodobenzenes / Q000737:chemistry; D007661:Ketoses / Q000138:chemical synthesis*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D006571:Heterocyclic Compounds; D007462:Iodobenzenes; D007661:Ketoses; D009942:Organometallic Compounds; C009406:tetrabutylammonium permanganate; D010165:Palladium
keywords: Oxidation; Sugar terminal alkyne; Sugar/heterocyclic(aryl)-1,2-diketone; Tetra-n-butylammonium permanganate