- Cobalt-Catalyzed Vinylic C-H Addition to Formaldehyde: Synthesis of Butenolides from Acrylic Acids and HCHO
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A carboxyl-assisted C-H functionalization of acrylic acids with formaldehyde to give butenolides is described. It is the first time that the addition of an inert vinylic C-H bond to formaldehyde has been achieved via cobalt-catalyzed C-H activation. The unique reactivity of the cobalt species was observed when compared with related Rh or Ir catalysts. γ-Hydroxymethylated butenolides were produced by the treatment of Na2CO3 after the catalytic reaction in one pot.
- Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 8359 - 8364
(2021/11/01)
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- Butenolide synthesis from functionalized cyclopropenones
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A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.
- Nguyen, Sean S.,Ferreira, Andrew J.,Long, Zane G.,Heiss, Tyler K.,Dorn, Robert S.,Row, R. David,Prescher, Jennifer A.
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p. 8695 - 8699
(2019/10/28)
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- A modular and scalable one-pot synthesis of polysubstituted furans
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One four all: Allyl dienol carbonates can be readily converted into diversely substituted furans by a one-pot four-step sequence featuring a palladium-catalyzed decarboxylative allylic alkylation, a microwave-mediated Cope rearrangement, a nucleophilic addition, and a dehydration reaction (see scheme). The protocol is operationally simple, highly flexible, and provides di-, tri-, and tetrasubstituted furans starting from readily available materials. Copyright
- Fournier, Jeremy,Arseniyadis, Stellios,Cossy, Janine
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supporting information; experimental part
p. 7562 - 7566
(2012/10/18)
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- Preparation and palladium-catalysed cross-coupling reactions of 3-and 4-tributylstannylfuran-2(5H)-ones
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Stannylfuranones 1 and 2 were prepared by ipso radical desulfurative stannylation of phenylsulfanylfuranones 3 and 16. Compounds 1 and 2 underwent Stille coupling reactions with aryl iodides to give 3- and 4-arylfuran-2(5H)-ones.
- Hollingworth, Gregory J.,Perkins, Gemma,Sweeney, Joseph
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p. 1913 - 1919
(2007/10/03)
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- Reductive Carbonylation of Acetylenes under Water-Gas Shift Reaction Conditions. Synthesis of Furan-2(5H)-ones from Terminal and Non-substituted Acetylenes
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Under water-gas reaction conditions terminal and non-substituted acetylenes are selectively converted into furan-2(5H)-ones by catalysis with a rhodium carbonyl cluster.
- Joh, Takashi,Nagata, Hiroyuki,Takahashi, Shigetoshi
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p. 1305 - 1308
(2007/10/02)
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- Preparation and reactions of 3-and 4-tributylstannyl-2-(5H)-furanones: Preparation of aryl furanones
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3- and 4-trialkylstannylfuranones (2) and (3) have been prepared by an interesting desulphurative stannylation reaction; 3- and 4-substituted 2-(5H)-Furanones (12) and (13) may be prepared via palladium-catalysed cross coupling of (2) and (3) with aryl iodides.
- Hollingworth, Gregory J.,Sweeney
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p. 7049 - 7052
(2007/10/02)
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