Aromatics from pyrones: para-substituted alkyl benzoates from alkenes, coumalic acid and methyl coumalate

Kraus, George A.; Riley, Sean; Cordes, Travis

doi:10.1039/c1gc15650k

Cited by 45 publications

(34 citation statements)

References 8 publications

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“…Methyl 4‐(phenoxymethyl)benzoate ( 3 j ) . White solid (22.0 mg, 45 %, Procedure B ; 26.3 mg from Cs 2 CO 3 (97.8 mg, 0.3 mmol) as a base at 50 °C, 55 %), a mixture of petroleum ether/ethyl acetate=20/1 (v/ v) as eluents for column chromatography.…”

Section: Methodsmentioning

confidence: 99%

“…All reactions were carried out under an itrogen atmosphere. Unless otherwise specified, NMR spectra were recorded in CDCl 3 on a 500 MHz (for 1 H), 471 MHz (for 19 F), and 126 MHz (for 13 C) spectrometer.A ll chemical shifts were reported in ppm relative to TMS (0 ppm for 1 HNMR) or PhCF 3 (À63.5 ppm for 19 FNMR) as an internal or external standard, respectively.T he HPLC experiments were carried out on aW ufeng LC-100 II instrument (column:S hodex, C18, 5 mm, 4.6 250 mm), and the yields of products were determined by using the corresponding pure compounds as the external standards, respectively.T he coupling constants were reported in Hertz (Hz). The following abbreviations were used to explain the multiplicities:s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, brs = broad singlet.…”

Section: Experimental Section General Informationmentioning

confidence: 99%

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Base‐Mediated O‐Arylation of Alcohols and Phenols by Triarylsulfonium Triflates

Ming

Tian

Zhang

2019

Chemistry An Asian Journal

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A mild and efficient protocol for O‐arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition‐metal‐free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron‐donating or electron‐withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base‐mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C−S bonds of triarylsulfonium cations to furnish the target products.

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Section: Methodsmentioning

confidence: 99%

Section: Experimental Section General Informationmentioning

confidence: 99%

Base‐Mediated O‐Arylation of Alcohols and Phenols by Triarylsulfonium Triflates

Ming

Tian

Zhang

2019

Chemistry An Asian Journal

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“…We have previously discussed and shown “star” diagrams for other example bioprivileged molecules including triacetic acid lactone (TAL) and 5‐hydroxymethylfurfural (HMF) that have received attention in the literature . An additional emerging bioprivileged molecule is coumalic acid, which can be produced by the dimerization of biological‐derived maleic acid . Potentially accessible products from coumalic acid have recently been presented as a computational case study .…”

Section: Bioprivileged Molecule Developmentmentioning

confidence: 99%

“…[9] An additional emerging bioprivileged molecule is coumalic acid, which can be produced by the dimerization of biological-derived maleic acid. [20,21] Potentially accessible products from coumalic acid have recently been presented as ac omputational case study. [17] Although each of these chemical intermediates are demonstrations of bioprivileged molecules, the development of ab ioprivileged molecule strategyc an best be advanced if it can be utilized to ChemSusChem 2019ChemSusChem , 12,2970ChemSusChem -2975 www.chemsuschem.org create am ore systematic approach for biobasedc hemicale xpansion.…”

Section: Bioprivileged Molecule Developmentmentioning

confidence: 99%

A Robust Strategy for Sustainable Organic Chemicals Utilizing Bioprivileged Molecules

Shanks

Broadbelt

2019

ChemSusChem

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Biobased chemicals will inevitably be an important part of a sustainable organic chemical industry. Current efforts in biobased chemicals are largely driven by opportunistic chemical product targets requiring complete technology development from feedstock to final product for a specific molecule. To enhance the development of biobased chemicals, it is important to create strategies that can be more systematic and can leverage advancements across multiple final products. Discussed here is the concept of bioprivileged molecules, which are chemical intermediates that have the potential to be efficiently converted into a range of product molecules that can both directly replace existing petrochemicals and are novel molecules that impart enhanced performance properties in end‐use applications.

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“…Produced from the dimerization of malic acid, it is a biorenewable synthon with diverse synthetic applications. [29][30][31][32][33][34][35][36] We recently discovered that MC can serve as 1,6-Michael acceptor, in the presence of certain nucleophiles. [37][38][39] Inspired by these findings, we began studying the nucleophilicity of the zwitterionic intermediates in the MBH catalytic pathway ( Figure 1).…”

Section: 10mentioning

confidence: 99%