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

Photomediated Radical Cascade Addition–Cyclization of N-Butenoyl Tetrahydroquinolines: Accessing Functionalized Julolidines DOI

Ajal P. Shaji,

Naremaddepalli S. Sudarshan,

Burkhard Koenig

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Herein, we describe the photomediated radical cascade addition-cyclization of N-butenoyl tetrahydroquinolines to access various functionalized julolidine-5-one. The scope methodology was illustrated with several sulfonyl chlorides and tetrahydroquinolines. Other precursors, such as trifluoromethyl, bromoacetonitrile, bromoacetates, etc., also worked efficiently, demonstrating broad utility method. Finally, large-scale synthesis sulfonyl-substituted julolidine-5-one downstream conversions synthesized julolidine derivatives were carried out illustrate synthetic methodology.

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
Synthesis of Acyl Cyclopentaquinolinones through Simultaneous Construction of the Heterocyclic Scaffold and Introduction of the Acyl Group DOI

Lian Xue,

Chang Gao, Xinying Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6292 - 6305

Published: April 16, 2024

Presented herein is an effective and concise synthesis of acyl cyclopentaquinolinone derivatives via the cascade reactions N-(o-ethynylaryl)acrylamides with α-diazo carbonyl compounds. The formation product involves a visible light-induced radical from compound followed by its addition onto acrylamide moiety to trigger double annulation, single-electron oxidation, β-elimination. To our knowledge, this first example in which scaffold was constructed along introduction group under light irradiation conditions. Compared literature methods for similar purpose, newly developed protocol has advantages such as readily accessible substrates, mild reaction conditions, valuable products, synthetic procedure, high sustainability. With all these merits, method expected find wide applications construction related heterocyclic skeletons.

Language: Английский

Citations

1
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