Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(15), С. 2916 - 2947

Опубликована: Янв. 1, 2024

In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.

Язык: Английский

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Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

Organic Letters, Год журнала: 2023, Номер 25(15), С. 2594 - 2599

Опубликована: Апрель 10, 2023

We herein demonstrate the acylsilane-directed Rh-catalyzed arene C–H bond alkylation with maleimides. The resulting derivatives were utilized in visible-light-induced intramolecular siloxycarbene-amide cyclization for synthesis of new tricyclic γ-lactams. In parallel, we also harnessed same acylsilane and maleimide units through [3 + 2] carbo-annulation by using Ru-catalysis. A wide range maleimides aroylsilanes used to establish broadness these transformations.

Язык: Английский

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Pd-Catalyzed Sequential Electrophilic Cyclization/Selective C–H Annulation Cascade: Synthesis of Isoxazole-Phthalimide-Fused Poly-Heterocyclics

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3214 - 3225

Опубликована: Фев. 21, 2024

Harnessing the organo-palladium intermediates generated from electrophilic cyclizations for tandem C–C bond construction is a challenging task but constitutes an excellent tool constructing complex motifs simpler substrates. We realize herein such cyclative annulation of alkynyl-oxime ethers with maleimides facile isoxazole-phthalimide hybrid through Pd(II) catalysis. This protocol features regio-selectivity in C–H selection, broad substrate scope, good functional group tolerance, and scalability. Necessary KIE & labeling studies give insight into reaction mechanism.

Язык: Английский

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Catalytic stereodivergent and simultaneous construction of axial and point chirality

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3308 - 3319

Опубликована: Янв. 1, 2024

An unprecedented ligand-enabled stereodivergent construction of both N–N axial and point chirality in a single step is reported.

Язык: Английский

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Chemo selective C-H alkylation of isoquinolones with maleimides: A combined experimental and computational case study

Molecular Catalysis, Год журнала: 2023, Номер 551, С. 113597 - 113597

Опубликована: Ноя. 7, 2023

Язык: Английский

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Ru(II)-Catalyzed C–H Activation/[4+2] Annulation of Sulfoxonium Ylide with Maleimide: Access to Fused Benzo[e]isoindole-1,3,5-trione

Organic Letters, Год журнала: 2024, Номер 26(32), С. 6830 - 6834

Опубликована: Авг. 5, 2024

A ruthenium-catalyzed C-H activation and a concomitant [4+2] annulation of sulfoxonium ylide with maleimide have been demonstrated. This tandem reaction results in the formation fused benzo[

Язык: Английский

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Redox‐Neutral Synthesis of Polycyclic Azaheterocycles via Cobalt‐Catalyzed Hydroarylation/Annulation of Maleimides

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(21), С. 3730 - 3735

Опубликована: Сен. 15, 2022

Abstract Herein, we report a cobalt‐catalyzed hydroarylation of maleimides followed by an annulation sequence for the synthesis polycyclic azaheterocycles in one pot. The reaction proceeds under redox‐neutral conditions and is compatible with various functional groups. Notably, as‐prepared product exhibits potential photophysical properties. magnified image

Язык: Английский

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Ni‐SPO‐Al Catalyzed Stereoselective C–H Alkenylation of Quinazolinones with Alkynes to Prepare trans‐Isomers

European Journal of Organic Chemistry, Год журнала: 2025, Номер 28(5)

Опубликована: Янв. 4, 2025

Abstract A stereoselective Ni−Al bimetal‐catalyzed C−H alkenylation of quinazolinones with alkynes has been successfully developed. Good selectivity Z‐type quinazolinone products was obtained using readily available substrates, which exhibits a trans‐configuration opposite to the conventional alkynylation reactions and improves diversity compounds. In addition, reaction process further explored through KIE other control experiments, possible mechanism proposed.

Язык: Английский

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Visible-Light-Induced Insertion of Siloxycarbene into Amide N–H Bonds: Synthesis of Carbinolamides from Acylsilanes and Amides

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1727 - 1732

Опубликована: Янв. 20, 2025

The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced siloxycarbene bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions a broad range amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable N- O-acetals excellent isolated yields. addition, chemoselective reveals robustness chemical transformation.

Язык: Английский

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Rhodium‐Catalyzed C8‐Alkenylation of Isoquinolones with Maleimides

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(30)

Опубликована: Июнь 15, 2023

Abstract An efficient Rh(III)‐catalyzed C−H alkenylation of N ‐protected isoquinolone with maleimides is reported. The carbonyl group acts as an inherent directing group. Various ‐substituents in the maleimide, including alkyl, aryl, and even H −OH, were well tolerated under developed reaction condition. This protocol showed broad substrate scope, good selectivity, excellent yields. Hammett plot also drawn to check effect substituents on progress.

Язык: Английский

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