title: Carbometalation-carboxylation of 2,3-allenols with carbon dioxide: a dramatic effect of halide anion.
abstract: The cyclic organometallic intermediates formed via CuCl-mediated highly regio- and stereoselective carbomagnesiation of 2,3-allenols with Grignard reagents may smoothly react with carbon dioxide to afford 2(5H)-furanones. A dramatic effect of the halide anion from the Grignard reagent (Br vs Cl) for CO(2) activation was observed. The reaction proceeded smoothly under mild conditions to afford the products in 58-93% yields.
authors: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China.
authors: Suhua
authors: S
authors: Li
authors: Bukeyan
authors: B
authors: Miao
authors: Weiming
authors: W
authors: Yuan
authors: Shengming
authors: S
authors: Ma
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000838:Anions; D002245:Carbon Dioxide / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000466:Alkadienes; D000838:Anions; D005663:Furans; D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D002245:Carbon Dioxide