Catalytic Decarbonylative Functionalization of C–H Bonds with Carboxylic Acids

Synlett, Journal Year: 2025, Volume and Issue: unknown

Published: March 31, 2025

Abstract Within the past decades, potential of transition-metal-catalyzed cross-coupling reactions using carboxylic acids as coupling partners has been subjected to extensive exploitation because natural abundance, ready availability, nontoxicity, stability, structural diversity, and low cost acids. Notably, recent years have witnessed intense research interest in combination decarbonylation with direct C–H bond functionalization presence transition-metal catalysts for formation various C–C bonds release CO. The approach presents a powerful alternative existing repertoire via formation. In this Account, we highlight our achievements development decarbonylative under catalysis. 1 Introduction 2 Arylation Aryl Carboxylic Acids 3 Alkenylation Alkenyl 4 Alkylation Alkyl 5 Conclusion Outlook

Language: Английский

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Transition Metal‐Catalyzed Direct Functionalization of Carbazoles

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

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Cobalt(III)-Catalyzed Directed C-7 Selective C–H Alkynylation of Indolines with Bromoalkynes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(29), P. 5411 - 5415

Published: July 17, 2023

A cobalt(III)-catalyzed directed C-7 alkynylation of indolines with easily accessible bromoalkynes has been developed. The reaction a broad substrate scope excellent yields and represents powerful route to the synthesis 7-alkynyl-substituted indolines. In addition, can be extended coupling N-aryl 7-azaindoles, highlighting synthetic practicability strategy.

Language: Английский

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Rhodium-catalysed additive-free carbonylation of benzamides with diethyl dicarbonate as a carbonyl source

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(14), P. 2744 - 2748

Published: Jan. 1, 2024

A rhodium-catalysed carbonylation of benzamides has been developed by employing diethyl dicarbonate as a stable and easy-to-handle carbonyl source.

Language: Английский

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Rh(III)‐Catalyzed Direct ortho Alkylation of Carbazoles with Nitroalkenes

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3461 - 3466

Published: Aug. 26, 2023

Abstract The Rh(III)‐catalyzed ortho alkylation of N ‐pyridylcarbazoles with nitroalkenes has been developed, furnishing a wide range 2‐(2‐nitroalkyl)carbazoles. Both aromatic and aliphatic participated in this reaction successfully. This protocol also proceeded well an indoline based substrate. Derivatization the representative nitroalkane product was described.

Language: Английский

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Rhodium-Catalyzed Intramolecular Acylation of 2-(Indol-1-yl)-benzoic Acids under Redox-Neutral Conditions

Synlett, Journal Year: 2023, Volume and Issue: 34(16), P. 1894 - 1898

Published: May 8, 2023

Abstract We developed a novel access to indoloindolone by rhodium-catalyzed intramolecular acylation of 2-(indol-1-yl)benzoic acids. This reaction proceeds via the in situ formation mixed anhydride under redox-neutral conditions. Preliminary mechanistic investigations revealed that formed participates C–H activation step, which is facilitated RhI catalyst. The utility this was demonstrated large-scale reaction.

Language: Английский

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Rhodium-catalyzed C6-Selective Alkoxycarbonylation of Pyridones

Chemistry Letters, Journal Year: 2022, Volume and Issue: 51(7), P. 775 - 777

Published: May 20, 2022

Abstract A novel method for the rhodium-catalyzed C6-selective alkoxycarbonylation of 2-pyridones is developed. This protocol offers a facile and direct synthetic route to 2-pyridone-6-carboxylates, which C–H functionalization has never been realized. The reaction proceeds without use stoichiometric additive by using dialkyl dicarbonates as alkoxycarbonyl source. can be successfully employed large-scale reaction.

Language: Английский

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Transition metal-catalyzed regioselective functionalization of carbazoles and indolines with maleimides

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(34), P. 6776 - 6783

Published: Jan. 1, 2022

An efficient and regioselective installation of succinimides on carbazoles indolines was achieved using a transition metal-catalyzed C–H functionalization strategy.

Language: Английский

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Rhodium-Catalyzed Decarbonylative Intramolecular Arylation of 2-(1H-Indole-1-carbonyl)benzoic Acids

Synlett, Journal Year: 2024, Volume and Issue: 35(17), P. 2037 - 2041

Published: Feb. 28, 2024

Abstract We developed a redox-neutral synthesis of isoindoloindolone via intramolecular arylation 2-(1H-indole-1-carbonyl)benzoic acids. This protocol facilitates the formation various substituted isoindoloindolones in yields ranging from 17% to 80%. Our mechanistic investigations indicate pivotal role NaI: iodide anion promotes desired isoindoloindolone, and sodium cation suppresses acylated byproducts, thereby enabling selective acceptable yields.

Language: Английский

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Rhodium-catalysed additive-free alkoxycarbonylation of indoles: 2,4,6-trimethylbenzoic acid-based carbonate anhydrides as a versatile alkoxycarboxyl source

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(16), P. 3209 - 3214

Published: Jan. 1, 2024

We developed a rhodium-catalysed alkoxycarbonylation of indoles, characterised by employing stable and easily available 2,4,6-trimethylbenzoic acid-based carbonate anhydrides.

Language: Английский

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