Synthesis of 1,7-Fused Indolines Tethered with Spiroindolinone Based on C–H Activation Strategy with Air as a Sustainable Oxidant

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1880 - 1897

Опубликована: Янв. 22, 2024

Herein, we present an efficient synthesis of 1,7-fused indolines tethered with a spiroindolinonyl moiety through the cascade reaction indolin-1-yl(aryl)methanimines diazo oxindoles. To best our knowledge, this is first example in which indoline skeleton was constructed along simultaneous introduction spiro element initiated by C–H bond activation indoline. In forming title product, substrate and coupling partner demonstrated unprecedented pattern latter acts as C1 synthon to participate construction spirocyclic scaffold reductive elimination key seven-membered Ru(II) species using air effective sustainable oxidant regenerate active catalyst. Moreover, studies on cytotoxicity selected products against several human cancer cell lines their potential lead compounds for development anticancer drugs. With notable features such simple economical substrates, pharmaceutically valuable sophisticated skeleton, mild conditions, cost-free oxidants, high efficiency, excellent compatibility diverse functional groups, scalability, method expected find wide applications related areas.

Язык: Английский

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Recent Advances in the Reaction of MBH Carbonates: Scope and Mechanism

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Июнь 27, 2024

Abstract In recent years, Morita‐Baylis‐Hillman (MBH) carbonates have been extensively used in domino reactions for the synthesis of novel cyclic and acyclic compounds. This review highlights progress made last decade a series compounds from an uncyclized reaction or annulation MBH carbonates, which demonstrates that excellent reactivity high research value as representative substrates organic synthesis. We hope summary understanding can inspire chemists to apply these design more efficient reactions, will be beneficial drug chemistry.

Язык: Английский

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Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones andortho-amino MBH carbonates to access dihydroquinolinone frameworks

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(4), С. 1034 - 1041

Опубликована: Янв. 1, 2023

A series of dihydroquinolinones have been synthesized via synergistic catalysis combining photolysis and Lewis base utilizing in situ generated ketenes ortho -amino MBH carbonates.

Язык: Английский

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Lewis Base Controlled (4 + 3) and (4 + 2) Annulations of MBH Carbonates with Benzofuran‐derived Azadienes: Access to Highly Substituted Benzofuro[3,2‐b]azepines and Spirotetrahydroquinolines

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4521 - 4527

Опубликована: Авг. 7, 2024

Abstract Catalyst‐controlled switchable (4+3) and (4+2) annulation reactions of Morita–Baylis–Hillman carbonates with benzofuran‐derived azadienes have been established. Employing PCy 3 as the catalyst, reaction could provide a variety synthetically useful benzofuro[3,2‐ b ]azepines in good yields (80–92%) excellent chemo‐ regioselectivities via cycloaddition reactions. Whereas changing catalyst from to DMAP, were switched construct highly substituted spirotetrahydroquinoline scaffolds three sequential stereocenters containing all‐carbon spiro‐quaternary efficiency diastereoselectivities (92–96% all cases>25:1 dr ) annulations. In addition, synthetic utility this method was further showcased by gram‐scale transformations product.

Язык: Английский

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Organophosphorus-Catalyzed “Dual-Substrate Deoxygenation” Strategy for C–S Bond Formation from Sulfonyl Chlorides and Alcohols/Acids

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8628 - 8635

Опубликована: Июнь 9, 2023

A green method to construct C-S bonds using sulfonyl chlorides and alcohols/acids via a PIII/PV═O catalytic system is reported. The organophosphorus-catalyzed umpolung reaction promotes us propose the "dual-substrate deoxygenation" strategy. Herein, we adopt strategy, which achieves deoxygenation of synthesize thioethers/thioesters driven by redox cycling. represents an operationally simple approach stable phosphine oxide as precatalyst shows broad functional group tolerance. potential application this protocol demonstrated late-stage diversification drug analogues.

Язык: Английский

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Regio- and Enantioselective N-Heterocyclic Carbene-Catalyzed Annulation of Aminoindoles Initiated by Friedel–Crafts Alkylation

Organic Letters, Год журнала: 2024, Номер 26(33), С. 6993 - 6998

Опубликована: Авг. 8, 2024

Chiral indoles annulated on the benzene ring are unique and significant in natural medicinal compounds. However, accessing these enantioenriched molecules has often been overlooked. The present study introduces an organocatalytic protocol to access compounds efficiently, demonstrated by substrate scope, functional group tolerance, using only 1 mol % of a chiral conjugated acid catalyst. Additionally, explores regioselectivity, gram-scale reactions, follow-up transformations, underscoring method's potential.

Язык: Английский

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P^III/P^V═O Redox Catalysis Mediated Thioesterification of Carboxylic Acids with Disulfides under Air Conditions

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 12, 2025

An efficient organophosphorus-catalyzed thiocarbonylation reaction of disulfides with carboxylic acids under air conditions was described. Various functional groups on and can be tolerated the present conditions, affording thioesters in good to excellent yields. This method exhibited chemoselectivity applied for late-stage functionalization drug molecules containing a acid group.

Язык: Английский

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Enantioselective Wittig Reactions Controlled by PIII/PV=O Redox Catalysis

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Фев. 3, 2025

Abstract The development of catalytic PIII/PV=O redox processes has transformed the Wittig reaction, traditionally plagued by stoichiometric phosphine oxide byproducts, into an efficient and more benign method for synthesizing alkenes. Recently, feasibility enantioselective catalysis was demonstrated using chiral catalysts, such as HypPhos. For example, atroposelective reaction Boc-MBH adducts, where endogenous base release facilitates ylide formation acid co-catalysis, allows enantiocontrol effective cycling, while catalyst-stereocontrolled reactions generally extend scope sustainability synthesis complex molecules. 1 Introduction 2 meso-Desymmetrizations 3 Atroposelective Catalysis 4 Conclusion

Язык: Английский

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A Sc(OTf)₃-catalyzed one-pot two-step approach for spiro-oxindole dihydropyridine derivatives initiated by N-olefination of MBH carbonates

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(9), С. 2294 - 2300

Опубликована: Янв. 1, 2023

An efficient one-pot, two-step, three-component reaction of isatin-derived MBH carbonates, sulfilimines, and epoxides was achieved, thus affording pharmaceutically important spiro-oxindole dihydropyridines.

Язык: Английский

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Atroposelective Arene‐Forming Wittig Reaction by Phosphorus P^III/P^V=O Redox Catalysis

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(37)

Опубликована: Июнь 28, 2024

Abstract The Wittig reaction is renowned as exceptionally versatile method for converting a diversity of aldehydes and ketones into alkenes. Recently, strategies chiral phosphine catalysis under P III /P V =O redox cycling emerged to render this venerable transformation stereoselective. Herein, we describe that enables the enantioselective synthesis pertinent biaryl atropisomers by means stereocontrolled arene‐forming reaction. Key process release an endogenous base from readily accessible tert ‐butyloxycarbonylated Morita–Baylis–Hillman adducts triggered catalyst intramolecularization, permitting mild atroposelective reactions. By strategy, broad obtained with up 94 : 6 enantioselectivity.

Язык: Английский

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