Selenonium ionic liquid as efficient catalyst for the Baylis–Hillman reaction

Lenardão, Eder J.; Feijó, Josiane de Oliveira; Thurow, Samuel; Perin, Gelson; Jacob, Raquel G.; Silveira, Cláudio C.

doi:10.1016/j.tetlet.2009.06.132

Cited by 59 publications

(13 citation statements)

References 33 publications

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“…An early application of Lewis‐acidic selenium salts was published in 2009 by Lenardão and colleagues. The addition of phenyl butyl ethyl selenonium tetrafluoroborate (PhBuEtSe + BF 4 – ) resulted in a significant acceleration of the Morita–Baylis–Hillman reaction of aldehydes and electron‐deficient alkenes . Ke, Yeung, and colleagues relied on similar selenonium cations in 2017 to catalyze the electrophilic bromination of arenes and aldol‐type reactions .…”

Section: Chalcogen Bondingmentioning

confidence: 99%

σ‐Hole Interactions in Catalysis

2020

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Noncovalent interactions like halogen, chalcogen, and pnictogen bonding are known for a very long time. During the last decade, these interactions have found different applications in catalysis. These forces are often called σ‐hole interactions which can be explained by the anisotropic distribution of the electron density around these atoms. In this MiniReview, we will present recent applications of halogen, chalcogen, and pnictogen bonding in catalysis and discuss experimental and computational investigations to gain more insights into the underlying mechanisms.

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Section: Chalcogen Bondingmentioning

confidence: 99%

σ‐Hole Interactions in Catalysis

2020

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“…To further explore this area and take benefit of the tellurium enhanced ChB property, we are currently designing tellurium‐based catalysts. Inspired by the works of Lenardão [18] and Yeung [19] who demonstrated that selenonium could act as organic Lewis acid and promote reaction, we designed new telluronium salts and studied them, and we report here their ChB ability and for the first time the high efficiency of these telluronium species as organocatalysts in typical reactions (Scheme 1, bottom).…”

Section: Methodsmentioning

confidence: 99%

Chalcogen‐Bonding Catalysis with Telluronium Cations

et al. 2021

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Chalcogen bonding results from non‐covalent interactions occurring between electrodeficient chalcogen atoms and Lewis bases. Among the chalcogens, tellurium is the strongest Lewis acid, but Te‐based compounds are scarcely used as organocatalysts. For the first time, telluronium cations demonstrated impressive catalytic properties at low loadings in three benchmark reactions: the Friedel–Crafts bromination of anisole, the bromolactonization of ω‐unsaturated carboxylic acids and the aza‐Diels–Alder between Danishefsky's diene and imines. The ability of telluronium cations to interact with a Lewis base through chalcogen bonding was demonstrated on the basis of multi‐nuclear (17O, 31P, and 125Te) NMR analysis and DFT calculations.

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“…In 2001, Afonso, Santos, and coworkers, and later Ko's group, reported that imidazolium‐based IL such as [BMIM][PF 6 ] appeared to accelerate significantly the rates of the Baylis–Hillman reaction. Since then, a number of different ILs supporting the Baylis–Hillman reaction has been reported, being most of them imidazolium‐based ILs . However, Aggarwal and co‐workers found that [BMIM][PF 6 ] in the presence of bases such as DABCO can also yield a side product by reaction of the deprotonated imidazolium salt at its C‐2 position with the aldehyde (Scheme B) .…”

Section: Introductionmentioning

confidence: 99%

A Preliminary Comparative Study of the Baylis–Hillman Reaction in Ionic Liquid Solution and Gelled Ionic Liquid

Schön

Saldías²,

Haldar

et al. 2019

Macromolecular Symposia

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Baylis–Hillman reaction in ionic liquid ([BMIM][PF6]) solution under stirring conditions and in the presence of a base (DABCO) can also be performed efficiently in non‐stirred gel phase upon gelation of the ionic liquid using a LMW gelator (i.e., (S)‐N‐(1‐oxo‐3‐phenyl‐1‐(tridecylamino)propan‐2‐yl)benzamide). In this preliminary study, the authors have compared both reaction media and the results showed similar behaviors. Interestingly, the ionogel is found to be slightly more effective affording the desired products with moderately higher yields within a reaction period of 24 h.

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Selenonium ionic liquid as efficient catalyst for the Baylis–Hillman reaction

Cited by 59 publications

References 33 publications

σ‐Hole Interactions in Catalysis

σ‐Hole Interactions in Catalysis

Chalcogen‐Bonding Catalysis with Telluronium Cations

A Preliminary Comparative Study of the Baylis–Hillman Reaction in Ionic Liquid Solution and Gelled Ionic Liquid

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