Transition metal-catalyzed C–H functionalizations of indoles

New Journal of Chemistry, Год журнала: 2021, Номер 45(31), С. 13692 - 13746

Опубликована: Янв. 1, 2021

This review summarises a wide range of transformations on the indole skeleton, including arylation, alkenylation, alkynylation, acylation, nitration, borylation, and amidation, using transition-metal catalyzed C–H functionalization as key step.

Язык: Английский

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Cobalt–N-Heterocyclic Carbene Complexes in Catalysis

ACS Catalysis, Год журнала: 2022, Номер 12(5), С. 3111 - 3137

Опубликована: Фев. 21, 2022

Cobalt–N-heterocyclic carbene (NHC) complexes have emerged as an attractive class of 3d transition metal catalysts for a broad range chemical processes, including cross-coupling, hydrogenation, hydrofunctionalization, and cycloaddition reactions. Herein, we present comprehensive review catalytic methods utilizing cobalt–NHC with focus on the catalyst structure, role NHC ligand, properties system, mechanism, synthetic utility. The survey clearly suggests that recent emergence well-defined may tremendous utility in design application reactions using more abundant metals.

Язык: Английский

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Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate

Chinese Chemical Letters, Год журнала: 2021, Номер 32(11), С. 3518 - 3521

Опубликована: Май 7, 2021

Язык: Английский

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Merging Directed C–H Activations with High-Throughput Experimentation: Development of Iridium-Catalyzed C–H Aminations Applicable to Late-Stage Functionalization

JACS Au, Год журнала: 2022, Номер 2(4), С. 906 - 916

Опубликована: Апрель 13, 2022

Herein, we report an iridium-catalyzed directed C–H amination methodology developed using a high-throughput experimentation (HTE)-based strategy, applicable for the needs of automated modern drug discovery. The informer library approach investigating accessible directing group chemical space, in combination with functional tolerance screening and substrate scope investigations, allowed generation reaction application guidelines to aid future users. Applicability late-stage functionalization complex drugs natural products, multiple deprotection protocols leading desirable aniline matched pairs, serve demonstrate utility method Finally, miniaturization nanomolar range highlights opportunities more sustainable decreased material consumption.

Язык: Английский

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Cp^xM(iii)-catalyzed enantioselective C–H functionalization through migratory insertion of metal–carbenes/nitrenes

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(34), С. 7264 - 7275

Опубликована: Янв. 1, 2021

In this review, we highlight the developments in chiral Cp x M( iii ) complexes or achiral complexes/chiral carboxylic acid-catalyzed enantioselective C–H functionalization reactions through migratory insertion of metal–carbenes/nitrenes.

Язык: Английский

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Practical Access to meta‐Substituted Anilines by Amination of Quinone Imine Ketals Derived from Anisidines: Efficient Synthesis of Anti‐Psychotic Drugs

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(21)

Опубликована: Март 21, 2023

Reversing the conventional site-selectivity of C-H activation provides efficient retrosynthetic disconnections to otherwise unreactive bonds. Described herein is Brønsted acid-catalyzed reaction that selectively performs meta-amination anisidines with aliphatic-, heterocyclic- and aromatic amines in a one-pot procedure. In addition dramatically simplifying synthesis meta-substituted anilines, our approach has advantage scalability remarkable functional group tolerance, including late-stage functionalization pharmaceutical compounds natural products. The control experiments detailed computational analysis provide insight into mechanism origin meta-selectivity. protocol extended challenging tri-aminated arenes successfully applied for 5-HT6 receptor antagonists, anti-psychotic drugs viz.. SB-214111, SB-258510, specifically, anti-schizophrenic drug SB-271046.

Язык: Английский

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Recent Advances in Cobalt‐Catalyzed, Directing‐Group‐Assisted C−H Bond Amidation Reactions

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(18), С. 4309 - 4331

Опубликована: Июль 22, 2021

Abstract C−N bond formation reactions have garnered a lot of interest in recent years due to the predominance nitrogen‐containing compounds most pharmacological medications. Since traditional approaches several limitations, transition metal‐catalyzed C−H amidation/amination process has arisen as more atom‐friendly option. Because there are so many distinct kinds bonds organic molecules, selective amidation always been challenge. In this scenario, directing‐group‐assisted received considerable attention, especially with inexpensive metal cobalt, its unique properties and efficiency. We summarize developments cobalt‐catalyzed directing‐group‐aided review. briefly discuss evolution directing group preferences their function site selection. magnified image

Язык: Английский

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Rhodium-Catalyzed Directed C(sp²)–H Bond Addition of 2-Arylindazoles to N-Sulfonylformaldimines and Activated Aldehydes

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(23), С. 15752 - 15759

Опубликована: Ноя. 13, 2020

Rhodium-catalyzed directed C-H functionalization of 2-arylindazoles with N-sulfonylformaldimines has been developed to provide a variety N-benzylarylsulfonamide derivatives good excellent yields. Different activated aldehydes like ethyl glyoxalate and 2,2,2-trifluoroacetaldehyde also efficiently underwent nucleophilic addition 2-arylindazoles. These selective transformations occur through the control C3 nucleophilicity indazole moiety. Mechanistic studies suggest that activation step may be rate-limiting step.

Язык: Английский

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Late‐Stage Amination of Drug‐Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium‐Catalyzed C−H Activation

Chemistry - A European Journal, Год журнала: 2021, Номер 27(72), С. 18188 - 18200

Опубликована: Окт. 21, 2021

The functionalization of C-H bonds, ubiquitous in drugs and drug-like molecules, represents an important synthetic strategy with the potential to streamline drug-discovery process. Late-stage aromatic C-N bond-forming reactions are highly desirable, but despite their significance, accessing aminated analogues through direct selective amination bonds remains a challenging goal. method presented herein enables wide array benzoic acids high selectivity. robustness system is manifested by large number functional groups tolerated, which allowed diverse marketed molecules. Furthermore, introduction handle enabled expeditious access targeted drug-delivery conjugates, PROTACs, probes for chemical biology. This rapid valuable analogues, combined operational simplicity applicability high-throughput experimentation has aid considerably accelerate drug discovery.

Язык: Английский

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Rhodium(III)‐Catalyzed Synthesis of Skipped Enynes via C(sp³)–H Alkynylation of Terminal Alkenes

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(11), С. 5693 - 5698

Опубликована: Янв. 10, 2021

Abstract The Rh III ‐catalyzed allylic C−H alkynylation of non‐activated terminal alkenes leads selectively to linear 1,4‐enynes at room‐temperature. catalytic system tolerates a wide range functional groups without competing functionalization other positions. Similarly, the vinylic α,β‐ and β,γ‐ unsaturated amides gives conjugated Z‐1,3‐enynes E‐enediynes.

Язык: Английский

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