A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride

Thopate, Yogesh; Singh, Rashmi; Rastogi, Sumit K.; Sinha, Arun K.

doi:10.1002/ajoc.201900513

Asian J Org Chem

2019

DOI: 10.1002/ajoc.201900513

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A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride

Yogesh Thopate

Rashmi Singh

Sumit K. Rastogi

et al.

Abstract: Scheme 1. Concept of ionic liquid-TBAF mediated regioselective conversion of β-bromohydrin into α-aryl ketone.

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Cited by 5 publications

(1 citation statement)

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“…The following supporting information can be downloaded at: . References [ 15 , 18 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ] are cited in the Supplementary Materials. 1 H and 13 C NMR spectra of the products synthesized in this work are available online.…”

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confidence: 99%

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

Yan

Zhang

et al. 2022

Molecules

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A practical method for the deoxygenation of α-hydroxyl carbonyl compounds under mild reaction conditions is reported here. The use of cheap and easy-to-handle Na2S·9H2O as the reductant in the presence of PPh3 and N-chlorosuccinimide (NCS) enables the selective dehydroxylation of α-hydroxyl carbonyl compounds, including ketones, esters, amides, imides and nitrile groups. The synthetic utility is demonstrated by the late-stage deoxygenation of bioactive molecule and complex natural products.

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mentioning

confidence: 99%

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

Yan

Zhang

et al. 2022

Molecules

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Arylsulfonic Anhydride as Thiol Surrogate for Sulfenylation of sp² C−H Bond Through De‐oxygenative Reduction with Neutral Ionic Liquid: Scope and Mechanistic Studies

Rastogi,

Equbal,

Kumar

et al. 2023

Adv Synth Catal

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We disclosed the dual role of neutral [Hmim]Br towards the direct conversion of arylsulfonic anhydride into arylthiol surrogate for the controlled and regioselective synthesis of 3‐sulfenylindoles from indole derivatives at rt. In addition, 2‐bromo‐3‐sulfenylindoles were synthesized in the presence of catalytic water at 50 °C in a cascade manner i. e. sulfenylation and bromination through de‐oxygenative reduction with [Hmim]Br in the absence of any additional brominating agent. The present method was also utilized for the sulfenylation of other heterocycles including azaindole, coumarin, naphthol, and pyrrole in good to excellent yields. Moreover, mechanistic investigations revealed this reaction was driven by imidazolium cation of neutral ionic liquid i. e. [Hmim]Br, which converts arylsulfonic anhydride into sulfenyl group for sulfenylation/bromination of sp2 C−H bond wherein an acidic ionic liquid [Hmim]pTSA is released as a by‐product.

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Cascade Multicomponent Reaction Involving Unprecedented Gould Jacobs‐Heck/Suzuki Coupling‐Hydrolysis‐Decarboxylation Reactions in One Pot: Rapid Synthesis of Hybrid Heterocyclic Molecules

et al. 2022

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Multicomponent reaction (MCR) has been one of the strong pillars of green chemistry. In this respect we herein report a multicomponent 5 step reaction in one pot by combining two known name reactions viz. Gould‐Jacobs reaction and Heck reaction for the synthesis of stilbene/biaryl‐quinolone hybrid molecules from readily available 4‐iodoaniline, (diethyl‐2‐(ethoxymethylene)malonate) EMME and styrene/aryl boronic acid. The use of diphenyl ether as a reaction solvent effectively mediated not only the Gould‐Jacobs reaction but surprisingly also the Heck reaction for the first time. Further, diphenyl ether also allowed easy isolation of crude product due to polar nature of the product via precipitation. The developed protocol thus offered unprecedented synthesis of hybrid molecules by converging five steps (Gould‐Jacobs reaction, Heck or Suzuki cross coupling, hydrolysis and decarboxylation) into one pot with simultaneous generation of C−C and C−N bonds besides cleavage of C−O and C−C bonds.

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A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride

Abstract: Scheme 1. Concept of ionic liquid-TBAF mediated regioselective conversion of β-bromohydrin into α-aryl ketone.

Cited by 5 publications

References 83 publications

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

Arylsulfonic Anhydride as Thiol Surrogate for Sulfenylation of sp² C−H Bond Through De‐oxygenative Reduction with Neutral Ionic Liquid: Scope and Mechanistic Studies

Cascade Multicomponent Reaction Involving Unprecedented Gould Jacobs‐Heck/Suzuki Coupling‐Hydrolysis‐Decarboxylation Reactions in One Pot: Rapid Synthesis of Hybrid Heterocyclic Molecules

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A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride

Abstract: Scheme 1. Concept of ionic liquid-TBAF mediated regioselective conversion of β-bromohydrin into α-aryl ketone.

Cited by 5 publications

References 83 publications

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

Arylsulfonic Anhydride as Thiol Surrogate for Sulfenylation of sp2 C−H Bond Through De‐oxygenative Reduction with Neutral Ionic Liquid: Scope and Mechanistic Studies

Cascade Multicomponent Reaction Involving Unprecedented Gould Jacobs‐Heck/Suzuki Coupling‐Hydrolysis‐Decarboxylation Reactions in One Pot: Rapid Synthesis of Hybrid Heterocyclic Molecules

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Product

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Arylsulfonic Anhydride as Thiol Surrogate for Sulfenylation of sp² C−H Bond Through De‐oxygenative Reduction with Neutral Ionic Liquid: Scope and Mechanistic Studies