Use of Silver Carbonate in the Wittig Reaction

Jedinak, Lukas; Rush, LaToya; Lee, Mijoon; Hesek, Dušan; Fisher, Jed F.; Boggess, Bill; Noll, Bruce C.; Mobashery, Shahriar

doi:10.1021/jo401972a

Cited by 19 publications

(5 citation statements)

References 35 publications

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“…Ag 2 CO 3 catalysts have drawn more and more attention because of their excellent catalytic activity in organic synthesis 17,18 and visible light photodegradation of organic contaminants 19,20 in environmental fields. In previous reports, most of Ag 2 CO 3 catalysts were single micron-sized crystalline grains 20−22 or nanorods 23 without a particular 3D hierarchical nanostructure, and they displayed deactivated photocatalic properties due to their photocorrosion.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Ag 2 CO 3 catalysts have drawn more and more attention because of their excellent catalytic activity in organic synthesis , and visible light photodegradation of organic contaminants , in environmental fields. In previous reports, most of Ag 2 CO 3 catalysts were single micron-sized crystalline grains − or nanorods without a particular 3D hierarchical nanostructure, and they displayed deactivated photocatalic properties due to their photocorrosion. , In order to significantly improve Ag 2 CO 3 particle adsorption performance and solve a serious photocorrosion problem, different strategies have been proposed, such as adding inhibitors in the photocatalytic reaction system , or coupling Ag 2 CO 3 with other materials like graphene oxide, Ag, , and UiO-66 .…”

Section: Introductionmentioning

confidence: 99%

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A Facile Method To Prepare Novel Ag₂O/Ag₂CO₃ Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function

Zhao

et al. 2017

ACS Sustainable Chem. Eng.

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A facile, green, and low-cost method to prepare novel Ag 2 O/Ag 2 CO 3 three-dimensional hollow flowerlike hierarchical microspheres has been demonstrated. The microspheres were obtained by simple injection of Na 2 CO 3 aqueous solution into AgNO 3 ethanol solution. The surface morphology of the microspheres was relatively smooth, trumpet flowerlike hole, and flowerlike shallow hole when the reaction temperature was 8, 25, and 70 °C, respectively. They were assembled by nanoparticles. The microsphere prepared at 25 °C was composed of 86.3% Ag 2 CO 3 and 13.7% Ag 2 O. The HTEM image indicates that the Ag 2 CO 3 microsphere is wrapped by a thin Ag 2 O layer, and there is a heterojunction between Ag 2 CO 3 and Ag 2 O. The study of the formation mechanism demonstrates the first example of using water-soluble Na 2 CO 3 as templates to prepare 3D hierarchical microstructures. The Ag 2 O/Ag 2 CO 3 microspheres prepared at 25 °C have excellent adsorption and photocatalysis activity for Congo red (CR). The adsorption behavior of the Ag 2 O/Ag 2 CO 3 microsphere follows the Langmuir isothermal adsorption model. The maximal adsorption capacity of the Ag 2 O/Ag 2 CO 3 microsphere was about 100.84 mg g −1 for CR in water. Here, 87.5% of CR was removed within 20 min under visible light irradiation at an initial concentration of CR of 80 mg L −1 with a photodegradation rate constant, k, of 0.06814. The radicals (O 2 •− ,•OH) and hole (h + ) were proved to be the active species for photocatalyzing CR. The microspheres were reused five times without distinct loss of photocatalysis activity, which indicated that they have stable photocatalysis activity. KEYWORDS: One step, Na 2 CO 3 template, Hierarchical microspheres, Ag 2 O/Ag 2 CO 3 , Water treatment

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Facile Method To Prepare Novel Ag₂O/Ag₂CO₃ Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function

Zhao

et al. 2017

ACS Sustainable Chem. Eng.

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“…Furthermore, the reliance of these methods on strongly basic conditions renders them incompatible with substrates having base-sensitive functionality. While some modifications have been introduced to allow for the use of weaker bases, the scope of those transformations is generally limited ( 11 , 12 ). An ideal solution to this problem would be to catalytically olefinate carbonyls under nonbasic conditions using an inexpensive and abundant olefinating reagent, such as olefins (alkenes) themselves.…”

Section: Introductionmentioning

confidence: 99%

Olefination of carbonyls with alkenes enabled by electrophotocatalytic generation of distonic radical cations

Steiniger

Lambert

2023

Sci. Adv.

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The conversion of carbonyls to olefins is a transformation of great importance for complex molecule synthesis. Standard methods use stoichiometric reagents that have poor atom economy and require strongly basic conditions, which limit their functional group compatibility. An ideal solution would be to catalytically olefinate carbonyls under nonbasic conditions using simple and widely available alkenes, yet no such broadly applicable reaction is known. Here, we demonstrate a tandem electrochemical/electrophotocatalytic reaction to olefinate aldehydes and ketones with a broad range of unactivated alkenes. This method involves the oxidation-induced denitrogenation of cyclic diazenes to form 1,3-distonic radical cations that rearrange to yield the olefin products. This olefination reaction is enabled by an electrophotocatalyst that inhibits back-electron transfer to the radical cation intermediate, thus allowing for the selective formation of olefin products. The method is compatible with a wide range of aldehydes, ketones, and alkene partners.

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“…One of the most popular methods to introduce double bonds in organic molecules was developed by George Wittig in 1953, which consists of a two-step reaction involving the formation of phosphonium ylides and its subsequent reaction with carbonyl moieties to yield the desired alkenes . However, the classical Wittig reaction often requires conditions such as usage of high temperature (≥100 °C) and strong bases. , The wide applicability of Wittig reaction in organic synthesis has led to the development of modified strategies that require milder reaction conditions. − As a result, Wittig reactions have been accomplished at milder bases and low temperature with many stabilized phosphonium ylides, especially for the synthesis of stilbene derivatives. − The introduction of visible light photocatalysis to carry out similar olefination reactions can potentially provide added advantages in terms of sustainability as well as help unravel newer mechanistic insights of the reaction. Here, we report the use of QDs as efficient visible-light photocatalysts at room temperature for performing olefination reactions in one pot.…”

Section: Introductionmentioning

confidence: 99%

Visible Light-Mediated Quantum Dot Photocatalysis Enables Olefination Reactions at Room Temperature

2023

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The ability of quantum dots (QDs) to photocatalyze organic reactions is gaining attention because of their distinct light harvesting properties over traditional precious metal- and small molecule-based catalysts. However, establishing the potency of QD photocatalysts in diverse and useful organic transformations, as well as deciphering the charge transfer mechanism, is essential to cement their place as an efficient photocatalyst in synthetic chemistry. Here, we report the use of QDs in efficiently catalyzing a series of olefination reactions under visible-light irradiation at room temperature (90% yield). Spectroscopic and electrochemical studies reveal intriguing insights on the charge transfer mechanism involved in QD-photocatalyzed olefination. Interestingly, the dual role of triphenylphosphineas a surface passivating agent and nucleophileturned out to be decisive in directing the charge transfer process from the QD to the reactant. Benzyl triphenylphosphonium bromide salt was accepting the electrons from the photoexcited QDs, thereby initiating the catalytic olefination reaction. QD-photocatalyzed olefination was demonstrated with formaldehyde as well, resulting in the formation of industrially relevant terminal alkene, namely styrene. Moreover, the environmentally friendly indium phosphide (InP) QD also photocatalyzed the olefination reaction under mild reaction conditions, which proves the practical suitability of our study. This work presents an attractive and efficient way to introduce double bonds in organic molecules using QDs and visible light at room temperature.

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Use of Silver Carbonate in the Wittig Reaction

Cited by 19 publications

References 35 publications

A Facile Method To Prepare Novel Ag₂O/Ag₂CO₃ Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function

A Facile Method To Prepare Novel Ag₂O/Ag₂CO₃ Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function

Olefination of carbonyls with alkenes enabled by electrophotocatalytic generation of distonic radical cations

Visible Light-Mediated Quantum Dot Photocatalysis Enables Olefination Reactions at Room Temperature

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Use of Silver Carbonate in the Wittig Reaction

Cited by 19 publications

References 35 publications

A Facile Method To Prepare Novel Ag2O/Ag2CO3 Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function

A Facile Method To Prepare Novel Ag2O/Ag2CO3 Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function

Olefination of carbonyls with alkenes enabled by electrophotocatalytic generation of distonic radical cations

Visible Light-Mediated Quantum Dot Photocatalysis Enables Olefination Reactions at Room Temperature

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A Facile Method To Prepare Novel Ag₂O/Ag₂CO₃ Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function

A Facile Method To Prepare Novel Ag₂O/Ag₂CO₃ Three-Dimensional Hollow Hierarchical Structures and Their Water Purification Function