Asymmetric transformations from sulfoxonium ylides

Chemical Science, Год журнала: 2021, Номер 13(5), С. 1192 - 1209

Опубликована: Дек. 8, 2021

Sulfoxonium ylides are important surrogates for diazo compounds, and their use in industry as safer alternatives has been evaluated during recent years. Beyond the known classical transformations, these have also used a surprising plethora of novel intrinsic chemical reactions, especially Bench stability handling an advantage this class organosulfur molecules. Despite this, efficient asymmetric specifically catalytic enantioselective versions, only recently reported, there specific reasons this. This perspective article covers topic from first studies up to latest advances, giving personal perspectives showing main challenges area coming

Язык: Английский

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Application of sulfoxonium ylide in transition-metal-catalyzed C-H bond activation and functionalization reactions

Tetrahedron, Год журнала: 2021, Номер 101, С. 132478 - 132478

Опубликована: Окт. 8, 2021

Язык: Английский

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Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(4)

Опубликована: Март 23, 2022

Abstract In recent years, the transition‐metal‐catalyzed functionalization reactions of sulfoxonium ylides have been explored extensively because their usefulness as carbene‐transfer agents, since they can produce metal carbenes through catalysis. Moreover, are safer and advantages simple handling good stability over other counterparts like diazo‐compounds. This review article attempts to highlight advances in metal‐catalyzed C−H ylides.

Язык: Английский

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Iridium-catalyzed B–H insertion of sulfoxonium ylides and borane adducts: a versatile platform to α-boryl carbonyls

Chemical Communications, Год журнала: 2019, Номер 56(3), С. 423 - 426

Опубликована: Дек. 4, 2019

Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields most cases (51 examples; up 84%). This practical scalable reaction showed broad substrate scope, high functional-group compatibility could be applied late-stage modification structurally complex drug compounds. Further synthetic applications were also demonstrated.

Язык: Английский

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Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

Angewandte Chemie International Edition, Год журнала: 2019, Номер 58(45), С. 16198 - 16202

Опубликована: Сен. 11, 2019

The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help a directing group has remained so far neglected area, despite advantageous safety profile ylides. Described herein are cyclizations onto benzenes, benzofurans N-p-toluenesulfonyl indoles in presence base HFIP, whereas pyrroles N-methyl undergo cyclization an iridium catalyst. Significantly, these two sets conditions chemospecific for each groups substrates.

Язык: Английский

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Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(36), С. 15554 - 15559

Опубликована: Апрель 30, 2020

Abstract The first example of enantioselective S−H insertion reactions sulfoxonium ylides is reported. Under the influence thiourea catalysis, excellent levels enantiocontrol (up to 95 % ee ) and yields 97 %) are achieved for 31 examples in aryl thiols α‐carbonyl ylides.

Язык: Английский

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Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides

Organic Letters, Год журнала: 2020, Номер 22(4), С. 1504 - 1509

Опубликована: Фев. 11, 2020

An unprecedented copper-catalyzed reaction of sulfoxonium ylides and anthranils is reported that enables an easy access to 2,3-diaroylquinolines through a [4+1+1] annulation. Copper-catalyzed homocoupling provided α,α,β-tricarbonyl ylides, which provides strategy extend the carbon chain C–C bond formation. The utility products as well mechanistic details process are presented.

Язык: Английский

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Cooperative copper-squaramide catalysis for the enantioselective N–H insertion reaction with sulfoxonium ylides

Chemical Science, Год журнала: 2021, Номер 12(21), С. 7453 - 7459

Опубликована: Янв. 1, 2021

The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from sulfur ylide, are described.

Язык: Английский

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On the Use of Differential Scanning Calorimetry for Thermal Hazard Assessment of New Chemistry: Avoiding Explosive Mistakes

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(37), С. 15798 - 15802

Опубликована: Авг. 17, 2020

Differential scanning calorimetry (DSC) is increasingly used as evidence to support a favourable safety profile of novel chemistry, or highlight the need for caution. DSC enables preliminary assessment thermal hazards potentially energetic compound. However, unlike other standard characterisation methods, which have well defined formats reporting data, current results hazard has shown concerning trends. Around half all in 2019 did not include experimental details required replicate procedure. Furthermore, analysis often only conducted unsealed crucibles, could lead misleading and dangerously incorrect conclusions. We specific issues with hazardous compounds currently organic chemistry literature provide simple "best practice" guidelines will give chemists confidence reported conclusions drawn from them.

Язык: Английский

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Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5572 - 5585

Опубликована: Апрель 21, 2023

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling α-keto sulfoxonium ylides with diselenides. The versatility electrochemical manifold enabled selenylation ample scope broad functional group tolerance, as well setting stage for modification complex bioactive Detailed mechanistic studies revealed that key C-Se bond was constructed using n-Bu4NI an electrolyte catalyst electrosynthetic protocol. Finally, desired showed excellent antimicrobial activity against Candida albicans, which can be identified lead further exploration.

Язык: Английский

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