C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2324 - 2338

Опубликована: Янв. 1, 2024

This review summarizes the most recent progress made in C–H bond activation-initiated spiroannulation reactions and their applications construction of structurally diverse biologically valuable spirocyclic scaffolds.

Язык: Английский

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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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Palladium-Catalyzed (3 + 2) Annulation of Aromatic Acids by C(sp³)–H Olefination and Decarboxylative Cross-Coupling Reaction

Organic Letters, Год журнала: 2024, Номер 26(7), С. 1338 - 1342

Опубликована: Фев. 9, 2024

A palladium-catalyzed (3 + 2) annulation of 2-methylbenzoic acid with maleimide using Ac-Leu-OH as a powerful ligand has been reported. Through site-selective γ-C(sp3)–H olefination reaction and sequential decarboxylative cross-coupling reaction, five-membered cyclic ring was obtained the final product. This novel features great site selectivity reactivity to generate various products in moderate good yields.

Язык: Английский

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Synthesis of γ-Lactams via Palladium-Catalyzed C(sp³)–H Bond Activation of Alkyl Sulfonamides with Substituted Alkenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 20, 2025

A methodology for the γ-butyrolactam scaffolds via ligand-enabled C(sp3)–H bond functionalization of sulfonamides with olefins has been demonstrated. The protocol found to be compatible several activated and unactivated olefins, desired lactams were formed in excellent yields. plausible mechanism described account lactamization reaction as well supported by mechanistic investigation including a 1H NMR study isolation palladacycle intermediate.

Язык: Английский

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Palladium-Catalysed Spiro-Cyclisation of Substituted Amino Acids with Maleimides via γ-C(sp³)–H Bond Activation

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

Achieving the site-selective functionalization of unactivated C(sp3)-H bonds remains a major challenge in organic synthesis. Herein, we report an efficient method for synthesis spiro pyrrolidine molecules via γ-C(sp3)-H bond activation substituted amino acids. A variety acid and alcohol derivatives, as well dipeptides, were functionalized using this method. Also, spirocyclization optically active substrates provided potential route preparing separable diastereomers pure enantiomeric form. Moreover, some mechanistic insights have been conducted to propose feasible reaction mechanism present reaction.

Язык: Английский

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Synthesis of lactones and lactams via C(sp³)–H bond functionalization

Chemical Society Reviews, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

In this review, we have showcased the diverse aspects of transition-metal catalysis, biocatalysis, and photocatalytic C(sp 3 )–H bond functionalization to access lactones lactams.

Язык: Английский

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Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(19), С. 4139 - 4144

Опубликована: Июль 2, 2024

Abstract A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, plausible mechanism for reaction proposed based on several control experiments, deuterium exchange previous reports.

Язык: Английский

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Ligand‐Enabled Pd‐Catalyzed sp³ C−H Macrocyclization: Synthesis and Evaluation of Macrocyclic Sulfonamide for the Treatment of Parkinson's Disease

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)

Опубликована: Июль 30, 2024

Abstract The development of simplified synthetic strategy to create structurally and functionally diverse pseudo‐natural macrocyclic molecules is highly appealing but poses a marked challenge. Inspired by natural scaffolds, herein, we describe practical concise ligand‐enabled Pd(II)‐catalyzed sp 3 C−H alkylation, olefination arylation macrocyclization, which could offer novel set sulfonamides. Interestingly, the potential ligand acceleration in activation also demonstrated an unprecedented enantioselective alkylation macrocyclization. Moreover, combination silico screening biological evaluation led identification spiro‐grafted sulfonamide 2 , showed promising efficacy for treatment Parkinson's disease (PD) mouse model through silent information regulator sirtuin (SIRT3).

Язык: Английский

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Maleimide-Dependent Rh(III)-Catalyzed Site-Selective Mono and Dual C–H Functionalization of 2-Arylbenzo[d]thiazole and Oxazole Derivatives

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

Опубликована: Дек. 3, 2024

The site-selective functionalization of aromatic compounds via C–H activation has emerged as a popular tool in organic synthesis. In this study, we report regioselective coupling maleimide to 2-arylbenzo[d]thiazoles the presence rhodium(III) catalyst. Depending upon nature substituent (R2-group) present substrate, either mono- or bis-1,4-addition products were observed methodology. case R2 = aryl, cyclohexyl, and tert-butyl, mono was observed, whereas substituents, such methyl, ethyl, benzyl, methyl thiophene, provided bis major products. Similar selectivity also 2-arylbenzo[d]oxazoles.

Язык: Английский

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Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Март 20, 2024

Abstract We report herein a palladium‐catalyzed, site‐selective cyclative annulation of o ‐alkynyl arylamides with maleimide for the stereoselective construction succinimide‐fused benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, downstream transformations. Control labeling experiments were conducted get insights into mechanism.

Язык: Английский

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