Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction

Malunavar, Shruti S.; Sutar, Suraj M.; Prabhala, Pavankumar; Savanur, Hemantkumar M.; Kalkhambkar, Rajesh G.; Aridoss, Gopalakrishnan; Laali, Kenneth K.

doi:10.1016/j.tetlet.2021.153339

Cited by 6 publications

(9 citation statements)

References 31 publications

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“…Collectively, these transformations enabled facile access to diverse libraries of small-molecule building blocks (Scheme 10 ). 20…”

Section: Expanding the Scope Of Metal-mediated Cross-coupling Reactio...mentioning

confidence: 99%

Section: Application Of Ils In Synthesis and Functionalization Of Het...mentioning

confidence: 99%

“…To demonstrate application, the synthesized epoxides were employed in the synthesis of a series of 2,3-disubstituted quinolines in [BMIM(SO 3 H)][OTf]/[BMIM][PF 6 ] (Scheme 54 ). 46…”

Section: ‘Name Reactions’and Other Widely Practiced Synthetic Transfo...mentioning

confidence: 99%

“…A two-step cyclization/cross-coupling protocol, starting from readily available 2-bromophenylaldimines, provided access to new libraries of small-molecule building blocks with increased complexity, via Suzuki, Heck, and Sonogashira reactions (Scheme 19 and Figure 3). 25 A one-pot sequential cyclization/cross-coupling protocol also proved viable, albeit with lower isolated yields. The 7-fluoro-7-iodochromenones were synthesized via halodediazoniation of chromenone-diazonium-BF 4 salts in BMIM-ILs, and further iodination with NIS furnished the 2,7-di-iodo derivatives (Scheme 23).…”

Section: Application Of Ils In Synthesis and Functionalization Of Het...mentioning

confidence: 99%

“…Libraries of functionalized cyclopropanes and oxiranes were prepared from enones and aldehydes, respectively, by using [PAIM][NTf 2 ] as a task-specific basic IL for in situ generation of sulfoxonium ylide from Me 3 S(O)I in BMIM-IL as solvent (Scheme 53 and Figure 6). 46 Scheme 49 Libraries of tetrahydropyrimidinones (-thiones) via the Biginelli reaction in ILs…”

Section: Synthesis Of Cyclopropanes and Oxiranes By The Corey-chaykov...mentioning

confidence: 99%

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Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs)

Laali

Kalkhambkar

Sutar

2021

Synlett

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The Account describes recent advances, from the authors’ laboratories, in the synthesis of diverse libraries of small-molecule building blocks employing ionic liquids (ILs). The ability of ILs to act as catalysts/promoters/solvents for electrophilic and onium ion chemistry, as well as in metal-mediated cross-coupling reactions, and the potential to sequence/hyphenate these methods, have opened up new opportunities for facile assembly of functional small molecules with increased complexity from readily available precursors. While Brønsted acidic IL/IL solvent mixtures are suitable media for carbocation and onium ion chemistry, piperidine-appended IL/IL solvent mixtures can successfully catalyze a variety of base-catalyzed reactions. Several widely practiced transformations including ‘name reactions’ were adapted and performed efficiently in ILs.1 Introduction2 Aryldiazonium Salts and Aryltriazenes as Coupling Partners in Metal-Mediated C–C Cross-Coupling Reactions in ILs3 Expanding the Scope of Metal-Mediated Cross-Coupling Reactions in ILs4 Application of ILs in Synthesis and Functionalization of Heterocycles5 Expanding the Scope of Amide Synthesis in ILs6 Generation and Chemistry of ‘Tamed’ Propargylic Cations in ILs7 Newer Nitration Methods for Arenes and Heteroarenes in ILs8 Halofunctionalization in ILs9 ‘Name Reactions’and Other Widely Practiced Synthetic Transformations in ILs9.1 The Biginelli Reaction9.2 Nitrile Synthesis by the Schmidt Reaction9.3 Rupe Rearrangement9.4 Synthesis of 1,3-Dioxanes via Prins Reaction in [BMIM(SO3H)][OTf]9.5 Synthesis of Cyclopropanes and Oxiranes by the Corey–Chaykovsky (CC) Reaction10 Conclusions and Closing Remarks

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“…Collectively, these transformations enabled facile access to diverse libraries of small-molecule building blocks (Scheme 10 ). 20…”

Section: Expanding the Scope Of Metal-mediated Cross-coupling Reactio...mentioning

confidence: 99%

Section: Application Of Ils In Synthesis and Functionalization Of Het...mentioning

confidence: 99%

“…To demonstrate application, the synthesized epoxides were employed in the synthesis of a series of 2,3-disubstituted quinolines in [BMIM(SO 3 H)][OTf]/[BMIM][PF 6 ] (Scheme 54 ). 46…”

Section: ‘Name Reactions’and Other Widely Practiced Synthetic Transfo...mentioning

confidence: 99%

Section: Application Of Ils In Synthesis and Functionalization Of Het...mentioning

confidence: 99%

Section: Synthesis Of Cyclopropanes and Oxiranes By The Corey-chaykov...mentioning

confidence: 99%

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Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs)

Laali

Kalkhambkar

Sutar

2021

Synlett

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Ultrasonication Assisted α‐Arylation of N‐heteroarenes Employing 1‐Aryltriazenes Promoted by Brønsted Acidic Ionic Liquid under Aerobic Conditions

et al. 2022

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An efficient and facile methodology for the synthesis of α‐arylated N‐heteroarenes was developed under aerobic conditions by means of ultrasound assistance, as well as conventional heating via a direct α‐arylation protocol employing Imidazolium based ionic liquids serving as both acid promoter and solvent. Structurally diverse N‐heteroarenes and 1‐aryltriazenes were evaluated for this reaction. This methodology has successfully provided a synthetic handle for various electron‐rich and electron‐deficient arylated N‐heteroarenes under metal and/or peroxide free conditions in good to excellent yields. The total synthesis of the known oxoisoaporphine class of alkaloids Menisporphine & Daurioxoisoporphine C was successfully accomplished using the current methodology as a key step in the total synthesis.

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Corey-Chaykovsky Reaction and Related Processes

Brière,

Perrio,

Reboul

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction

Cited by 6 publications

References 31 publications

Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs)

Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs)

Ultrasonication Assisted α‐Arylation of N‐heteroarenes Employing 1‐Aryltriazenes Promoted by Brønsted Acidic Ionic Liquid under Aerobic Conditions

Corey-Chaykovsky Reaction and Related Processes

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