LiAlH4/silica chloride as a new chemoselective system for reduction of carbonyl compounds and phosphine oxides

Khalilzadeh, Mohammad A.; Hosseini, Abolfazl; Tajbakhsh, Mahmood; Mohannazadeh, Farajollah

doi:10.1007/bf03246152

Cited by 7 publications

(1 citation statement)

References 11 publications

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“…The terminal hydroxyl group exhibits better surface and interface properties and is compatible with metals and inorganic substances. Therefore, the conversion of COOH to OH is of interest [29,30] and is commonly achieved using sodium borohydride (NaBH 4 ) systems [31].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of the Novel High-Performance Hydroxyl-Terminated Liquid Fluoroelastomer

Chen

et al. 2023

Polymers

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Functional liquid fluoroelastomers are in high demand in new energy fields. And these materials have potential applications in high-performance sealing materials and as electrode materials. In this study, a novel high-performance hydroxyl-terminated liquid fluoroelastomer (t-HTLF) with a high fluorine content, temperature resistance, and curing efficiency was synthesised from a terpolymer of vinylidene fluoride (VDF), tetrafluoroethylene (TFE), and hexafluoropylene (HFP). A carboxyl-terminated liquid fluoroelastomer (t-CTLF) with controllable molar mass and end-group content was first prepared from a poly(VDF-ter-TFE-ter-HFP) terpolymer using a unique oxidative degradation method. Subsequently, an efficient “one-step” reduction of the carboxyl groups (COOH) in t-CTLF into hydroxyl groups (OH) was achieved via the functional-group conversion method using lithium aluminium hydride (LiAlH4) as the reductant. Thus, t-HTLF with a controllable molar mass and end-group content and highly active end groups was synthesised. Owing to the efficient curing reaction between OH and isocyanate groups (NCO), the cured t-HTLF exhibits good surface properties, thermal properties, and chemical stability. The thermal decomposition temperature (Td) of the cured t-HTLF reaches 334 °C, and it exhibits hydrophobicity. The oxidative degradation, reduction, and curing reaction mechanisms were also determined. The effects of solvent dosage, reaction temperature, reaction time, and ratio of the reductant to the COOH content on the carboxyl conversion were also systematically investigated. An efficient reduction system comprising LiAlH4 can not only achieve an efficient conversion of the COOH groups in t-CTLF to OH groups but also the in situ hydrogenation and addition reactions of residual double bonds (C=C) groups in the chain, such that the thermal stability and terminal activity of the product are improved while maintaining a high fluorine content.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of the Novel High-Performance Hydroxyl-Terminated Liquid Fluoroelastomer

Chen

et al. 2023

Polymers

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Highly Chemoselective Reduction of Phosphine Oxides through Electrophilic Activation of the P=O Bond with Anhydride

Jin

Xiao

et al. 2023

Eur J Org Chem

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A highly chemoselective reduction of phosphine oxides was demonstrated under transition‐metal‐free and alkaline reaction conditions. During the reaction, P=O bond was firstly electrophilically activated by an anhydride and subsequently reduced by the versatile and cheap NaH, which was strengthened by 15‐crown‐5. By this strategy, a variety of phosphine oxides including those bearing functional groups such as methyl, methoxyl, phenyl, fluorine, chlorine, bromine, iodine, trifluoromethyl, nitrile, ester, alkenyl, alkynyl and heterocycles were transformed readily into the corresponding phosphines in good to high yields. This work represents an efficient method for reducing phosphine oxides forming phosphines.

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Silica-supported LiHSO4 as a highly efficient, heterogeneous and reusable catalytic system for the solvent-free synthesis of β-enaminones and β-enamino esters

Hasaninejad

Zare

Mohammadizadeh

et al. 2010

JICS

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LiAlH4/silica chloride as a new chemoselective system for reduction of carbonyl compounds and phosphine oxides

Cited by 7 publications

References 11 publications

Synthesis and Properties of the Novel High-Performance Hydroxyl-Terminated Liquid Fluoroelastomer

Synthesis and Properties of the Novel High-Performance Hydroxyl-Terminated Liquid Fluoroelastomer

Highly Chemoselective Reduction of Phosphine Oxides through Electrophilic Activation of the P=O Bond with Anhydride

Silica-supported LiHSO4 as a highly efficient, heterogeneous and reusable catalytic system for the solvent-free synthesis of β-enaminones and β-enamino esters

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