title: Thermodynamically Favorable Synthesis of 2-Oxazolidinones through Silver-Catalyzed Reaction of Propargylic Alcohols, CO2, and 2-Aminoethanols.
abstract: Development of catalytic routes to incorporate CO2 into carbonyl compounds at mild conditions remains attractive and challenging. Herein, a one-pot three-component cascade reaction of terminal propargylic alcohols, CO2 , and 2-aminoethanols through Ag(I) -based catalysis is reported for the synthesis of carbonyl compounds through C-O/C-N bond formation. This thermodynamically favorable route can be ingeniously regulated to afford a wide range of 2-oxazolidinones along with concurrent production of α-hydroxyl ketone derivatives in excellent yields and selectivity. Preliminary mechanistic studies indicate that such a process proceeds through successive formation of α-alkylidene cyclic carbonate, β-oxopropylcarbamate, and 2-oxazolidinones.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P.R. China.|State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan, 030001, P. R. China.
authors.forename: Qing-Wen
authors.initials: QW
authors.lastname: Song
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P.R. China.
authors.forename: Zhi-Hua
authors.initials: ZH
authors.lastname: Zhou
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P.R. China.
authors.forename: Mei-Yan
authors.initials: MY
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan, 030001, P. R. China.
authors.forename: Kan
authors.initials: K
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan, 030001, P. R. China.
authors.forename: Ping
authors.initials: P
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan, 030001, P. R. China.
authors.forename: Jia-Yao
authors.initials: JY
authors.lastname: Xun
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P.R. China. heln@nankai.edu.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071, P.R. China. heln@nankai.edu.cn.
authors.forename: Liang-Nian
authors.initials: LN
authors.lastname: He
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002245:Carbon Dioxide / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D019856:Ethanolamine / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D000480:Alkynes; D023303:Oxazolidinones; D020005:Propanols; D002245:Carbon Dioxide; D012834:Silver; D019856:Ethanolamine; C028255:propargyl alcohol
keywords: carbon dioxide fixation; heterocycles; homogeneous catalysis; multicomponent reaction; synthetic methods