Transition-metal-catalyzed C–H bond alkylation using olefins: recent advances and mechanistic aspects

Chemical Society Reviews, Год журнала: 2022, Номер 51(17), С. 7358 - 7426

Опубликована: Янв. 1, 2022

Transition metal catalysis has contributed immensely to C-C bond formation reactions over the last few decades, and alkylation is no exception. The superiority of such methodologies traditional evident from minimal reaction steps, shorter times, atom economy while also allowing control regio- stereo-selectivity. In particular, hydrocarbonation alkenes grabbed increased attention due its fundamental ability effectively selectively synthesise a wide range industrially pharmaceutically relevant moieties. This review attempts provide scientific viewpoint systematic analysis recent developments in transition-metal-catalyzed various C-H bonds using simple activated olefins. key features mechanistic studies involved these transformations are described briefly.

Язык: Английский

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Nickel-catalyzed C(sp2)–H alkynylation of free α-substituted benzylamines using a transient directing group

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 110901 - 110901

Опубликована: Янв. 1, 2025

Язык: Английский

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Radical 1‐Fluorosulfonyl‐2‐alkynylation of Unactivated Alkenes

Angewandte Chemie International Edition, Год журнала: 2021, Номер 61(12)

Опубликована: Дек. 27, 2021

Sulfonyl fluorides have found widespread use in chemical biology and drug discovery. The development of synthetic methods for the introduction sulfonyl fluoride moiety is therefore importance. Herein, a transition-metal-free radical 1,2-difunctionalization unactivated alkenes via FSO

Язык: Английский

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Recent advances in the synthesis of 2,3-fused quinazolinones

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(32), С. 6293 - 6313

Опубликована: Янв. 1, 2022

As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.

Язык: Английский

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Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications

Molecules, Год журнала: 2023, Номер 28(5), С. 2136 - 2136

Опубликована: Фев. 24, 2023

Hypervalent iodine reagents are in high current demand due to their exceptional reactivity oxidative transformations, as well diverse umpolung functionalization reactions. Cyclic hypervalent compounds, known under the general name of benziodoxoles, possess improved thermal stability and synthetic versatility comparison with acyclic analogs. Aryl-, alkenyl-, alkynylbenziodoxoles have recently received wide applications efficient for direct arylation, alkenylation, alkynylation mild reaction conditions, including transition metal-free conditions photoredox metal catalysis. Using these reagents, a plethora valuable, hard-to-reach, structurally complex products can be synthesized by convenient procedures. The review covers main aspects chemistry benziodoxole-based aryl-, alkynyl-, alkenyl- transfer preparation applications.

Язык: Английский

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The Alkynylative Difunctionalization of Alkenes

Chemistry - A European Journal, Год журнала: 2022, Номер 28(61)

Опубликована: Авг. 1, 2022

Abstract Given alkynyl group is an important functional unit, a variety of efficient methods have been developed to construct alkynyl‐containing compounds. Among them, the alkynylative difunctionalization alkenes one most straightforward and strategies for preparing these compounds so has made great progress in recent years, including catalytic asymmetric manner. However, there no comprehensive review summarize studies. This aimed at comprehensively summarizing alkenes, which presented terms alkynylation‐initiated alkynylation‐terminated difunctionalizations alkenes. We hope that this will help encourage more researchers further explore field.

Язык: Английский

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Palladium-Catalyzed Tandem Nucleophilic Addition/C–H Functionalization of Anilines and Bromoalkynes for the Synthesis of 2-Phenylindoles

Organic Letters, Год журнала: 2023, Номер 25(9), С. 1409 - 1414

Опубликована: Март 1, 2023

A novel and efficient palladium-catalyzed annulation of anilines with bromoalkynes for the synthesis 2-phenylindoles has been described. This approach features excellent regio- stereoselectivities good functional group tolerance. Preliminary mechanistic studies indicate that undergo anti-nucleophilic addition to generate (Z)-N-(2-bromo-1-phenylvinyl) anilines, followed by sequential C-H functionalization deliver different substituted 2-phenylindoles. method provides potential applications construction various biologically active compounds.

Язык: Английский

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Diverse reactivity of alkynes in C–H activation reactions

Chemical Communications, Год журнала: 2022, Номер 58(74), С. 10262 - 10289

Опубликована: Янв. 1, 2022

The metal–carbon bond generated through C–H activation is a key organometallic intermediate, which could be further functionalized with various reacting partners. Among the coupling partners used in metal-catalysed activation, alkynes occupy prominent position on account of their varied reactivity.

Язык: Английский

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Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Angewandte Chemie International Edition, Год журнала: 2022, Номер 62(12)

Опубликована: Дек. 30, 2022

The C-H functionalization strategy provides access to valuable molecules that previously required convoluted synthetic attempts. Dual unsymmetrical functionalization, with a single bifunctional reagent, is an effective tactic. Propargyl alcohols (PAs), despite containing reactive C≡C bond, have not been explored as building blocks via oxidative cleavage. Annulations activation are versatile and synthetically attractive strategy. We disclose PA new reagent for dual of biphenylamine regioselectively annulated outcomes. On tuning the conditions, annulation bifurcated towards unusual cyclization. This method accommodates wide range PAs showcases late-stage diversification some natural products.

Язык: Английский

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Pd-catalysed C–H alkynylation of benzophospholes

Chemical Communications, Год журнала: 2024, Номер 60(20), С. 2792 - 2795

Опубликована: Янв. 1, 2024

A palladium-catalysed C2–H alkynylation of benzophospholes with alkynyl bromides has been developed to afford the corresponding phosphole-alkyne conjugations in good yields.

Язык: Английский

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