Palladium‐Catalyzed Direct Alkynylation of Carbazoles with Alkynyl Bromides DOI

Jyothis Dharaniyedath,

Vikash Kumar, Parthasarathy Gandeepan

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(40)

Published: June 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.

Language: Английский

An Expedient Flow Chemistry Approach to Substituted 1,4‐Dimethylcarbazoles DOI Creative Commons
Jennifer R. Baker, Michael C. Hamilton, Cecilia C. Russell

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(13)

Published: March 28, 2025

Abstract A simple, expedient continuously scalable flow chemistry synthesis of a range 1,4‐dimethylcarbazoles from substituted indoles and 2,5‐hexanedione in the presence K‐10 (montmorillonite clay) is reported. Optimization conditions led to development an in‐house K‐10/sand Omnifit TM catalyst column that at 140 °C 0.4 mL.min −1 afforded >90% conversion selected indole desired 1,4‐carbazole. This equates ca 80 mg.h production rate. The reaction was tolerant electron donating but not withdrawing indoles.

Language: Английский

Citations

0
Transition Metal‐Catalyzed Direct Functionalization of Carbazoles DOI
Vikash Kumar,

S. Sudharsan,

Lusina Mantry

et al.

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

Citations

0
Substituent-controlled regioselective arylation of carbazoles using dual catalysis DOI Creative Commons
Muhammad Shahid, Perumal Muthuraja, Purushothaman Gopinath

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(4), P. 753 - 758

Published: Dec. 20, 2023

Controlled regioselective mono- and di-arylation of carbazoles using dual palladium–photoredox catalysis.

Language: Английский

Citations

4
Palladium‐Catalyzed Direct Alkynylation of Carbazoles with Alkynyl Bromides DOI

Jyothis Dharaniyedath,

Vikash Kumar, Parthasarathy Gandeepan

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(40)

Published: June 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.

Language: Английский

Citations

1