Carbon–Carbon Bond Cleavage for Late-Stage Functionalization

Chemical Reviews, Год журнала: 2023, Номер 123(22), С. 12313 - 12370

Опубликована: Ноя. 9, 2023

Late-stage functionalization (LSF) introduces functional group or structural modification at the final stage of synthesis natural products, drugs, and complex compounds. It is anticipated that late-stage would improve drug discovery's effectiveness efficiency hasten creation various chemical libraries. Consequently, products a productive technique to produce product derivatives, which significantly impacts biology development. Carbon-carbon bonds make up fundamental framework organic molecules. Compared with carbon-carbon bond construction, activation can directly enable molecular editing (deletion, insertion, atoms groups atoms) provide more efficient accurate synthetic strategy. However, selective unstrained still one most challenging projects in synthesis. This review encompasses strategies employed recent years for cleavage by explicitly focusing on their applicability functionalization. expands current discourse reactions providing comprehensive overview types bonds. includes C-C(sp), C-C(sp2), C-C(sp3) single bonds; double triple bonds, focus catalysis transition metals organocatalysts. Additionally, specific topics, such as ring-opening processes involving three-, four-, five-, six-membered rings, are discussed, exemplar applications these techniques showcased context bioactive molecules discovery. aims shed light advancements field propose potential avenues future research realm

Язык: Английский

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Weak Chelation-Assisted C4-Selective Alkylation of Indoles with Cyclopropanols via Sequential C–H/C–C Bond Activation

Organic Letters, Год журнала: 2022, Номер 24(32), С. 6000 - 6005

Опубликована: Авг. 10, 2022

A Rh-catalyzed weak chelation-guided C4-alkylation of indoles has been accomplished using cyclopropanols as an alkylating agent via the cascade C–H and C–C bond activation. The substrate scope, functional group tolerance, late-stage mutation drug molecules are important practical features.

Язык: Английский

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Progress in Transition‐Metal‐Catalyzed Synthesis of Benzo‐Fused Oxygen‐ and Nitrogen Heterocyclic Compounds from Benzoic Acids

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(2), С. 124 - 141

Опубликована: Янв. 10, 2023

Abstract Transition‐metal‐catalyzed oxidative annulation reactions can be used to synthesize various benzo‐fused oxygen‐ and nitrogen‐containing heterocyclic compounds from benzoic acids. This review deals with publications the past 15 years that focus on modifications of reaction conditions variations coupling reagents this end, as well development methods characterized by sustainability, a broad range substrates, high tolerance functional groups in constructing skeletons are commonly found drugs bioactive molecules. summarizes categorizes mechanisms reagents. magnified image

Язык: Английский

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Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

ChemistrySelect, Год журнала: 2023, Номер 8(32)

Опубликована: Авг. 23, 2023

Abstract Cyclopropanols, due to their particular chemistry, can participate in various synthetic reactions with retention or cleavage of the strained three‐membered ring. Direct cross‐coupling ring‐opening reaction such molecules access organic compounds, as ketones has great importance medicinal chemistry and material sciences. Hence, coupling reaction/cyclization cyclopropanols for constructing new valuable presence a transition metal catalyst under metal‐free conditions is described this context. The features are discussed, mechanisms challenging highlighted.

Язык: Английский

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Three‐Component Synthesis of Benzofuran‐3(2H)‐ones with Tetrasubstituted Carbon Stereocenters via Rh(III)‐Catalyzed C−H/C−C Bond Activation and Cascade Annulation

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(15), С. 2540 - 2545

Опубликована: Июнь 25, 2022

Abstract An one‐pot three‐component synthesis of benzofuran‐3(2 H )‐ones with tetrasubstituted carbon stereocenters from salicylaldehydes, cyclopropanols, and alkyl alcohols via Rh(III)‐catalyzed C−H/C−C bond activation cascade annulation has been successfully developed. magnified image

Язык: Английский

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Rhodium-Catalyzed C2-Alkylation of Indoles with Cyclopropanols Using N,N-Dialkylcarbamoyl as a Traceless Directing Group

Organic Letters, Год журнала: 2022, Номер 24(37), С. 6745 - 6749

Опубликована: Сен. 11, 2022

An efficient rhodium-catalyzed synthesis of C2-alkylated NH-free indoles has been achieved from substituted and cyclopropanols. The reaction allows the various products in good to excellent yield. Important features method include use a N,N-dialkylcarbamoyl group as traceless directing group, C-H/C-C bond functionalization, functional tolerance, broad scope, pyrrolo[1,2-a]indole, identification potential intermediates.

Язык: Английский

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Catalytic Enantioselective [4+1]-Annulation of Carboxylic Acids with Cyclopropenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 12, 2025

An efficient asymmetric synthesis of 3-vinylphthalides has been accomplished through rhodium-catalyzed [4+1]-annulation arylcarboxylic acids with cyclopropenes involving C–H bond functionalization. The method exhibited excellent compatibility for various functional groups and offered diverse substituted in yield enantioselectivity. Synthetic application control experiments were also performed to demonstrate the utility understand reaction pathway.

Язык: Английский

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Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 694 - 694

Опубликована: Янв. 1, 2025

Язык: Английский

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Trichloroacetonitrile-Mediated Oxidation of Sulfides and Benzylic C–H Bonds via Photoexcited Radical Reactions under Clean Conditions

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 27, 2025

The protocol using only trichloroacetonitrile (CCl3CN) or CCl3CN/methanol to achieve oxidation of sulfides and benzylic C-H bonds in open air was established. Highly selective sulfoxides efficient were realized under clean mild conditions, respectively. main features this are a wide substrate scope, high yields, gram-scale preparation, conversion various pharmaceutical molecules. reactions performed light irradiation, the mechanism demonstrated involve radical process. This provides sustainable straightforward method for bonds.

Язык: Английский

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Synthesis of 3‐Hydroxyfluorenones Based on the Cascade Reaction of Aryl Enaminones with Benzyl Substituted Cyclopropanols

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 4, 2025

Comprehensive Summary Presented herein is a novel synthesis of 3‐hydroxyfluorenones through the cascade reaction aryl enaminones with benzyl substituted cyclopropanols. The formation product initiated by introduction an enone moiety onto enaminone cyclopropanol as homoenolate precursor C−H bond activation, followed intramolecular enamine Michael addition, enol amine elimination and aromatization‐driven oxidative dehydrogenation. To our knowledge, this should be first example for specific 3‐hydroxyfluorenone derivatives via simultaneous both indenone phenol scaffolds C−H/C−C/C−N activation three C−C formation. In general, newly developed protocol features easily accessible substrates, synthetically pharmaceutically valuable products, unique pathway, good compatibility various functional groups ready scalability.

Язык: Английский

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