- Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols
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A straightforward aerobic oxidative esterification of aryl aldehydes with alcohols has been developed for the synthesis of substituted esters by employing vitamin B1 as a cost-effective, metal-free, and eco-friendly NHC catalyst. Air is used as a green terminal oxidant. The reaction is a useful addition to the existing NHC-catalytic oxidative esterification.
- Chu, Xue-Qiang,Ge, Danhua,Luo, Xin-Long,Xu, Pei,Yu, Zi-Lun
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supporting information
p. 30937 - 30942
(2021/11/19)
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- Metal-free, regio- and stereoselective synthesis of linear (E)-allylic compounds using C, N, O, and S nucleophiles
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A variety of allylic acetates and derivatives were synthesized by an efficient two-step protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)- isomer as the sole adduct. This process tolerates several functional groups including halogen-containing molecules, and it is general for weak oxygen, carbon, nitrogen, and sulfur nucleophiles. Furthermore, adducts were obtained in good to excellent yields.
- Huang, Xiaojun,Fulton, Brandon,White, Kana,Bugarin, Alejandro
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p. 2594 - 2597
(2015/06/16)
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- Palladium-catalyzed allylic fluorination
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Mild and rapid: The title reaction is presented and its applicability to 18F radiolabeling is demonstrated (see scheme; TBAF=tetra-n- butylammonium fluoride, THF=tetrahydrofuran, dba=dibenzylideneacetone). The use of p-nitrobenzoate as the leaving group is significant to the success of this catalytic organometallic fluorination process. A range of allylic fluorides were synthesized by this method. Copyright
- Hollingworth, Charlotte,Hazari, Amaruka,Hopkinson, Matthew N.,Tredwell, Matthew,Benedetto, Elena,Huiban, Mickael,Gee, Antony D.,Brown, John M.,Gouverneur, Veronique
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supporting information; experimental part
p. 2613 - 2617
(2011/05/03)
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- N-heterocyclic carbene-mediated oxidative esterification of aldehydes: Ester formation and mechanistic studies
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An unexpected N-heterocyclic carbene-catalyzed esterification of α,β-unsaturated aldehydes including aromatic aldehydes with reactive cinnamyl bromides in the presence of air oxygen or MnO2 as an oxidant is described. In the presence of oxygen, halogenated and electron-deficient aldehydes react smoothly to furnish esters in good yields. Great efforts have been made on mechanistic studies to deduce a plausible mechanism, based on the experimental results and isotopic labeling experiment.
- Maji, Biswajit,Vedachalan, Seenuvasan,Ge, Xin,Cai, Shuting,Liu, Xue-Wei
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experimental part
p. 3016 - 3023
(2011/06/20)
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- Migration of aryl groups from silicon to carbon in α,β-epoxysilanes. A new model for hypervalent silicon study
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The reaction of (2R,3R)-3-(triphenylsilyl)glycidol (1) with n-Bu4NF·3H2O in THF, followed by treatment of the product with p-nitrobenzoyl chloride yields (2S)-glycidol p-nitrobenzoate (4) and trans-cinnamyl p-nitrobenzoate (6) in a ratio of 1:1.5. The reaction of (R)Si-(2R,3R)- or (R)Si-(2S,3S)-3-[(methyl)(phenyl)(1-naphthyl)silyl]-glycidols, 7 or 8 respectively, with n-Bu4NF·3H2O affords mixtures of the respective glycidol, trans-cinnamyl alcohol and 3-(1-naphthyl)allyl alcohol. No significant difference in the product distribution in reaction of these two diasteromers was observed.
- Achmatowicz, Barbara,Jankowski, Pawel,Wicha, Jerzy,Zarecki, Andrzej
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p. 227 - 230
(2007/10/03)
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