Study on the Reactivity of Aldehydes in Electrolyzed Ionic Liquids: Benzoin Condensation – Volatile Organic Compounds (VOCs) <i>vs.</i> Room Temperature Ionic Liquids (RTILs)

Chiarotto, Isabella; Feroci, Marta; Orsini, Monica; Feeney, Michelle; Inesi, Achille

doi:10.1002/adsc.201000555

Cited by 22 publications

(14 citation statements)

References 29 publications

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“…The in situ generation of NHCs can also be conveniently performed by electrochemical reduction of azolium precursors, forming molecular H 2 as a by-product (Scheme 2). [61][62][63][64][65][66][67] In situ generation of NHCs resulting from the deprotonation of supported imidazolium salts on silica or on organic polymeric materials (Fig. 7) can be performed with neutral bases, such as Et 3 N or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) [68][69][70][71] or ionic bases, such as t-BuONa or NaH (Scheme 3).…”

Section: Synthesis Of Nhcs and Their Supported Analoguesmentioning

confidence: 99%

N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis

et al. 2013

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The chemistry of N-heterocyclic carbenes (NHCs) has witnessed tremendous development in the past two decades: NHCs have not only become versatile ligands for transition metals, but have also emerged as powerful organic catalysts in molecular chemistry and, more recently, in metal-free polymer synthesis. To understand the success of NHCs, this review first presents the electronic properties of NHCs, their main synthetic methods, their handling, and their reactivity. Their ability to activate key functional groups (e.g. aldehydes, esters, heterocycles, silyl ketene acetals, alcohols) is then discussed in the context of molecular chemistry. Focus has been placed on the activation of substrates finding analogies with monomers (e.g. bis-aldehydes, multi-isocyanates, cyclic esters, epoxides, N-carboxyanhydrides, etc.) and/or initiators (e.g. hydroxy- or trimethylsilyl-containing reagents) employed in such "organopolymerisation" reactions utilizing NHCs. A variety of metal-free polymers, including aliphatic polyesters and polyethers, poly(α-peptoid)s, poly(meth)acrylates, polyurethanes, or polysiloxanes can be obtained in this way. The last section covers the use of NHCs as structural components of the polymer chain. Indeed, NHC-based photoinitiators, chain transfer agents or functionalizing agents, as well as bifunctional NHC monomer substrates, can also serve for metal-free polymer synthesis.

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Section: Synthesis Of Nhcs and Their Supported Analoguesmentioning

confidence: 99%

N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis

et al. 2013

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“…This organocatalytic strategy was successfully applied to many organic reactions, including for example the benzoin condensation, [31][32][33] esterification and amidation of benzaldehydes and cinnamaldehydes, [34][35][36][37][38][39][40][41] synthesis of γbutyrolactones, [42][43] synthesis of 1,3-diketones, [44] etc..…”

Section: Introductionmentioning

confidence: 99%

Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer

et al. 2019

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The cathodic reduction of dicationic imidazolium bromides, whose spacer is either an aliphatic chain or a xylyl group, leads to the formation of the corresponding N‐heterocyclic carbenes (NHCs), which were isolated as the corresponding thiones, after reaction with elemental sulfur. The behaviour of the dications was compared with the corresponding monocations. The behaviour of dicarbenes depends on the nature of the spacer. This study evidenced that dicarbenes deriving from xylyl dications are less stable than the corresponding aliphatic ones (giving lower yields in thiones), due to a debenzylation reaction. On the other hand, the yields in thiones starting from aliphatic dications are higher than the corresponding monocations, suggesting a cooperative reduction at the electrode of the two imidazolium moieties. The cathodic process was confirmed using the co‐electrogenerated hydrogen to reduce 2,2,2‐trifluoroacetophenone to the corresponding alcohol.

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“…Using this galvanostatic control yields from moderate (32%) to very high (92%) were obtained for the purified products. 15,16 The existence of NHC derived from {[Bmim]AcO} was later determined at 120ºC by cyclic voltammetry (Scheme 1). 17 Thiazolium and imidazolium cations from ionic liquids as pre-catalysts in benzoin condensation-a mini review…”

Section: Formation Of N-heterocyclic Carbenes From Ionic Liquids Usedmentioning

confidence: 99%

Thiazolium and imidazolium cations from ionic liquids as pre-catalysts in benzoin condensation–a mini review

Villamizar-Mogotocoro

Urbina-González

2018

JAPLR

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Synthesis of benzoins and their substituted derivatives is well known for more than a century since the original work of Liebig and Wöhler. This important strategy to create new CC bonds now uses N-heterocyclic carbenes (NHC) as catalysts, mainly derived from azolium cations obtained from different ionic liquids. Although numerous reports have been published to date, this article covers just the main aspects in the NHC formation from azolium pre-catalysts.

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Study on the Reactivity of Aldehydes in Electrolyzed Ionic Liquids: Benzoin Condensation – Volatile Organic Compounds (VOCs) vs. Room Temperature Ionic Liquids (RTILs)

Cited by 22 publications

References 29 publications

N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis

N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis

Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer

Thiazolium and imidazolium cations from ionic liquids as pre-catalysts in benzoin condensation–a mini review

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