Transition Metal‐Catalyzed Direct Functionalization of Carbazoles

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Апрель 29, 2025

Abstract Carbazoles are an important class of nitrogen‐containing heterocycles found in diverse natural products, bioactive molecules, and functional materials. Their broader applications have driven extensive research into their synthesis functionalization. Among various approaches, transition metal‐catalyzed C−H activation has emerged as a powerful tool for direct functionalization, offering regioselectivity, efficiency, sustainability. This review comprehensively summarizes advancements functionalization carbazoles. Various catalytic systems employing palladium, ruthenium, rhodium, nickel, cobalt, copper, iron enabled alkylation, alkenylation, acylation, arylation, alkynylation, heteroatom incorporation These methodologies late‐stage diversification opened avenues accessing structurally complex carbazole derivatives with tailored properties. The aims to provide comprehensive guide researchers exploring via activation, highlighting key mechanistic insights, scope, emerging trends this field.

Язык: Английский

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Ru(II)‐Catalyzed Selective C—H Alkynylation of Isoquinolones, Quinazolones and Phthalazinones with Bromoalkynes

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(15), С. 1686 - 1690

Опубликована: Март 15, 2024

Comprehensive Summary A new, selective Ru(II)‐catalyzed alkynylation reaction of isoquinolones, quinazolones and phthalazinones with readily available bromoalkynes has been developed. This enables the construction a new C(sp 2 )‐C(sp) bond through C—H activation C—Br functionalization, offers an effective route to synthesizing highly valuable alkynylated isoquinolone, quinazolone phthalazinone derivatives wide substrate scope high selectivity.

Язык: Английский

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Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(9), С. 985 - 989

Опубликована: Дек. 26, 2023

Comprehensive Summary A Ru(II)‐catalyzed ortho allylation reaction of N ‐aryl‐7‐azaindole with readily available 2‐methylidene cyclic carbonate has been developed. This is an effective pathway for synthesizing 7‐azaindole derivatives a wide scope substrates and high yields. In addition, the method can be extended to other heterocyclic compounds several carbonates, highlighting practicality this strategy synthesis.

Язык: Английский

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Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1840 - 1846

Опубликована: Фев. 8, 2024

Abstract Herein, we report a chemo‐ and regioselective Rh‐catalyzed redox C7‐spiroannulation reaction of N ‐benzo[ d ]imidazole indolines with maleimides, resulting in series indoline fused azaspirocycles up to 92% yield. The synthetic utility is demonstrated by the synthesis highly functionalized nitrogen‐containing spiropolycyclic skeletons. annulation could also be performed maleic esters acrylates. products were purified simple filtration. Rh catalyst can recycled, at gram‐scale using 0.5 mol% catalyst, which makes this protocol potentially applicable industry. Moreover, efficient post‐modification pharmaceutical molecules demonstrates its practicability.

Язык: Английский

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Regiodivergent C–H Alkynylation of 2-Arylthiazoles Switched by Ru^II and Pd^II Catalysis

Chemical Communications, Год журнала: 2024, Номер 60(52), С. 6679 - 6682

Опубликована: Янв. 1, 2024

Two complementary regiodivergent C–H alkynylations of 2-arylthiazoles are reported.

Язык: Английский

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Palladium‐Catalyzed Direct Alkynylation of Carbazoles with Alkynyl Bromides

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(40)

Опубликована: Июнь 18, 2024

Abstract Carbazole derivatives are vital in medicinal and materials chemistry, yet accessing diverse substitutions remains challenging. Here, we introduce a regioselective approach for C1 C8 alkynylation of carbazoles via palladium‐catalyzed C−H activation. This method provides direct route to mono‐ di‐alkynylated derivatives, addressing the scarcity alkynylated carbazole‐based materials. Our study broadens synthetic toolbox carbazole functionalization, offering potential applications optoelectronics, bio‐imaging, beyond, while contributing developing sustainable activation methodologies.

Язык: Английский

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Co(III)-Catalyzed C6-Selective C–H Activation/Pyridine Migration of 2-Pyridones with Propiolates

Organic Letters, Год журнала: 2023, Номер unknown

Опубликована: Дек. 21, 2023

A versatile Co(III)-catalyzed C6-selective C–H activation/pyridine migration of 2-pyridones with available propiolates as coupling partners was demonstrated. This method features high atom economy, excellent regioselectivity, and good functional group tolerance by employing an inexpensive Co(III) catalyst under mild reaction conditions. Moreover, gram-scale synthesis late-stage modifications pharmaceuticals were performed to prove the effectiveness these synthetic approaches.

Язык: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

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Co(III) or Ru(II)-Catalyzed Selective C–H Alkynylation of 2-Pyridones and Their Derivatives with Bromoalkynes

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

Опубликована: Дек. 5, 2024

We successfully reported selective C–H alkynylation of 2-pyridones with bromoalkynes under the catalysis Co(III) or Ru(II). The reaction used easily accessible instead high-valent iodine alkynes. There is a broad substrate scope good yields. In addition, 2-pyridone can be as weakly directing group for proximal aryl bond. This method offers an efficient approach synthesizing diverse derivatives, yielding alkynylated products up to 95% yield (>40 examples).

Язык: Английский

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Cobalt Catalysis: C7 Alkynylation of Indolines with a Bromoalkyne

Synthesis, Год журнала: 2023, Номер 56(05), С. 751 - 757

Опубликована: Ноя. 28, 2023

Abstract A method for the cobalt-catalyzed C-7 alkynylation of indolines with (bromoethynyl)triisopropylsilane under mild conditions is described, leading to a diverse range alkynylated in good excellent yields. Kinetic isotope studies indicate that formation cobaltacycle might be turnover-limiting step. Additionally, gram-scale synthesis and oxidation an indoline indole have been carried out successfully

Язык: Английский

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