Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions

He, Xuhua; Wang, Xinyan; Tse, Ying-Lung Steve; Ke, Zhihai; Yeung, Ying‐Yeung

doi:10.1002/anie.201806965

Cited by 81 publications

(62 citation statements)

References 59 publications

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“…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 . In both cases, the authors propose a chalcogen‐bond activation, but no detailed mechanistic investigations have been reported so far.…”

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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“…More recently, Yeung and Ke and their co‐workers elegantly developed a highly chemo‐ and diastereoselective bromo‐carbocyclization using a trisubstituted selenonium tetrafluoborate salt as the organic Lewis acid catalyst together with a proof‐of‐concept study . The optimized selenonium tetrafluoborate salt 62 can be prepared by reacting bis[4‐(trifluoromethyl)phenyl]selane with methyl iodide and AgBF 4 in 1,2‐dichloroethane and used in this reaction after recrystallization from dichloromethane and diethyl ether.…”

Section: Reaction Classesmentioning

confidence: 99%

Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

Maji

2019

Adv Synth Catal

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Ther eview is aimeda tdescribingt he advances in electrophilic "iranium" ion-triggered Friedel-Crafts-type alkylation for polyenec yclizations. Owing to the greatp otential of halo-, seleno-and sulfeno-functionalized Friedel-Crafts alkylated compounds,n umerous catalytic methodsh aveb een developed in either racemico re nantiopure forms. More importantly,t hese arene-alkylated or polyenecyclized productsc ontaining halo,s eleno ands ulfeno functionality couldb eu seful in further synthetic planning to access biologically active molecules and natural productsw ith highly complex architectures. Starting from aw ide range of classicalL ewis acids, Brønsted acids and Lewis bases through to the very recently developed halogen bondc atalysts (XB-cat.), selenonium cations as Lewis acids etc. are utilized to access these types of compounds.M orer ecently, some of the co-operative catalytic systems such as phosphite-thiourea, sulfonic acid-phosphoramidite, sulfonic acid-selenophosphoramide,s ulfonic acidanion binding thiourea, etc. catalyzing highly diastereo-and enantioselective polyene cyclizations have also been described. Thec onfigurational stability,r eactivity and selectivity of three-membered cationic

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“…[8] Examples involving noncovalent organocatalysis still remain underrepresented. [9] In 2017, first such cases employing neutral sulphur-based or cationic selenium-basedc atalysts were reported by Matile [10] and our group, [5a] with the reactions involving the reductiono f quinolines anda nS N 1-based carbon-carbon bond formation, and similaro nes were being investigated later on. [5b, 11] Recently,o ur group could confirmt he superior performance of cationic chalcogen bondingc atalysts versusn eutralo nes in a direct comparison, [12] and we also reported the first activation of an itro group, [5c] using tellurium-based dicationic catalysts.…”

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confidence: 99%

Carbonyl Activation by Selenium‐ and Tellurium‐Based Chalcogen Bonding in a Michael Addition Reaction

Wonner

Steinke

Vogel

et al. 2020

Chemistry A European J

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In the last years the use of chalcogen bonding-the noncovalent interaction involving electrophilic chalcogen centers-in noncovalentorganocatalysis has received increasedi nterest, particularly regarding the use of intermolecularL ewisa cids. Herein, we present the first use of tellurium-based catalysts for the activation of ac arbonyl compound (and only the second such activation by chalcogen bondingi ng eneral). As benchmark reaction, the Michael-typea ddition between trans-crotonophenone and 1-methylindole (and its derivatives) was investigated in the presence of various catalyst candidates. Whereas non-chalcogen-bonding reference compounds werei nactive, strong rate accelerations of up to 1000c ould be achieved by bidentate triazolium-basedc halcogen bond donors, with product yields of > 90 %w ithin 2h of reaction time. Organotellurium derivatives were markedly more active than their seleniuma nd sulphur analogues and non-coordinatingc ounterions like BAr F 4 provide the strongest dicationic catalysts.Chalcogen bonding [1] denotes the attractive interaction between electrophilicc halcogen centers and Lewis bases.

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Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions

Cited by 81 publications

References 59 publications

σ‐Hole Interactions in Catalysis

σ‐Hole Interactions in Catalysis

Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

Carbonyl Activation by Selenium‐ and Tellurium‐Based Chalcogen Bonding in a Michael Addition Reaction

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