Lewis base-assisted Lewis acid-catalyzed selective alkene formation via alcohol dehydration and synthesis of 2-cinnamyl-1,3-dicarbonyl compounds from 2-aryl-3,4-dihydropyrans

刘昌会,; 潘彬,; 顾彦龙,

doi:10.1016/s1872-2067(15)61084-1

Cited by 19 publications

(11 citation statements)

References 65 publications

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“…To overcome this issue, we performed the water elimination reaction using an AlCl 3 /PPh 3 catalytic system in N,N-dimethylformamide solvent that allowed for complete elimination (Figure 3). 32 This two-step procedure showed several advantages: (i) a good global yield was obtained >80%. (ii) Only extractions/ washing were required to purify the final product.…”

Section: Preparation Of the 34-dimethoxystyrene Monomermentioning

confidence: 99%

Increasing the Scale and Decreasing the Cost of Making a Catechol-Containing Adhesive Polymer

et al. 2023

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Achieving adhesive bonding in wet environments remains a significant challenge in both day-to-day life and industrial applications. Inspired by how marine shellfish stick to rocks, a wide variety of innovative polymer adhesives containing catechol moieties have been developed by several research groups. Despite displaying impressive performance, these adhesives have not yet emerged on the market. Difficulties associated with translating small-scale academic research to industrial production have persisted. In this paper, we focus our attention on poly(vinylcatechol-styrene), a biomimetic polymer that has shown considerable bonding in both dry and underwater conditions. Herein, we tackled three issues to help bring this polymer beyond academic laboratories: monomer sourcing, polymerization processes, and deprotection steps. Thus, we propose a new route to produce poly(vinylcatecholstyrene) made of (i) a 3,4-dimethoxystyrene monomer preparation from 3′,4′-dimethoxyacetophenone, a low-cost and highavailability reagent, (ii) a suspension polymerization to yield the intermediate poly(3,4-dimethoxystyrene-styrene) at the large scale, and (iii) an iodocylohexane-induced methyl cleavage to obtain the final poly(vinylcatechol-styrene). In our laboratory, we could synthesize this adhesive polymer at up to 60 g scales, avoided harsh reaction conditions, and reduced the cost of the polymer by half. Cost calculations are described both for materials only and also when considering labor and energy. An unexpected bonus was improved performance in both dry and wet conditions.

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Section: Preparation Of the 34-dimethoxystyrene Monomermentioning

confidence: 99%

Increasing the Scale and Decreasing the Cost of Making a Catechol-Containing Adhesive Polymer

et al. 2023

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“…[1][2][3] There are some ways to synthesize this motif (Scheme 1A), for instance, the elimination reaction of halo-or hydroxyl-substituted tetrahydronaphthalenes, intramolecular annulation of phenyl alkenes or alkynes, partial hydrogenation of naphthalene and partial oxidation of tetrahydronaphthalene. [4][5][6][7][8][9][10][11][12] However, these methods usually suffer from substrate scope limitation and harsh reaction conditions. In consideration of the atom and step economy, the direct utilization of readily available styrenes to construct 1,2dihydronaphthalene is a promising way.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Oxidative [4+2] Annulation of Different Styrenes toward the Synthesis of 1,2-Dihydronaphthalenes

et al. 2022

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A [4+2] annulation of two different styrenes to construct polysubstituted 1,2-dihydronaphthalenes was achieved. This transformation proceeded smoothly under electrochemical oxidative conditions without metal catalysts and external oxidants. A series of polysubstituted 1,2-dihydronaphthalenes were obtained with high regioselectivity and diastereoselectivity. Moreover, polysubstituded 1,2-dihydronaphthalenes were further transformed to polysubstituted 1,2,3,4-tetrahydronaphthalenes and polysubstituted naphthalenes, which showed great potentials in synthetic application.

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“…The photo conversion performance of nanofluids was also enhanced as a consequence of the promising stability. Previously, we developed Lewis acid catalysis induced ring-opening reactions of 2-butoxy-3,4-dihydropyran (DP) with various of nucleophiles, and among them, mercaptans quite stood out which were able to react with DP with high regio-selectivity and yields. − Inspired by this reaction, we envision that DP deemed to be able to link onto the surface of SH containing silica with the aid of a Lewis acid. Moreover, owing to the coordination effect of the acetylacetonate moiety in the DP molecule, copper can be anchored on the surface of this modified silica with the purpose of thermal conductivity enhancement.…”

Section: Introductionmentioning

confidence: 99%

Novel Silica Filled Deep Eutectic Solvent Based Nanofluids for Energy Transportation

Liu

Fang

Liu

et al. 2019

ACS Sustainable Chem. Eng.

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Liquid range of nanofluids is a crucial parameter as it intensively determines their application temperature scope. Meanwhile, improved thermal conductivity and stability are of great significances and comprise the main fundamental research topics of nanofluids. In this work, 2butoxy-3,4-dihydropyran (DP), produced from a convenient one-pot three-component reaction in water, was employed as dual lipophilic brusher and metal nanoparticle anchor. It was found that DP was able to enhance the dispersing ability and thermal conductivity of SiO 2 nanoparticle filled deep eutectic solvent (DES) based nanofluids simultaneously. The key to the success of this protocol mainly relies on the electrophilic property and acetylacetonate moiety of DP, which ensures the formation of DP surficial modified and copper nanoparticle coated silica. Molecular dynamics simulation revealed that the hydrogen bonding effect between base solvent and alkane chain of nanoparticle was responsible for the enhanced affinity, which thus resulted in an improved stability. Viscosities of the nanofluids dropped within a certain range owing to the ruin of hydrogen bonding association among solvent molecules resulted by the hydrogen bonding effect between nanoparticle and solvent. Thermal conductivity of the copper modified silica filled DES nanofluids exhibits a maximum 13.6% enhancement, which demonstrated the advantages of this chemical covalent protocol. Additionally, study upon viscosity and convective heat transfer coefficient of the nanofluids with varies types of silica nanoparticle and DES base solvents indicated that a 24.9% heat transfer coefficient enhancement was gained that further revealed the superiority of this protocol.

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Lewis base-assisted Lewis acid-catalyzed selective alkene formation via alcohol dehydration and synthesis of 2-cinnamyl-1,3-dicarbonyl compounds from 2-aryl-3,4-dihydropyrans

Cited by 19 publications

References 65 publications

Increasing the Scale and Decreasing the Cost of Making a Catechol-Containing Adhesive Polymer

Increasing the Scale and Decreasing the Cost of Making a Catechol-Containing Adhesive Polymer

Electrochemical Oxidative [4+2] Annulation of Different Styrenes toward the Synthesis of 1,2-Dihydronaphthalenes

Novel Silica Filled Deep Eutectic Solvent Based Nanofluids for Energy Transportation

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