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

Green Synthesis of 3,4‐Unsubstituted Isoquinolones through Rhodium(III)‐Catalyzed C−H Activation and Annulation in Ethanol DOI
Vikash Kumar, Parthasarathy Gandeepan

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(44)

Published: Sept. 27, 2023

Abstract A mild and convenient synthesis of 3,4‐unsubstituted isoquinolones has been achieved from N ‐methoxybenzamides vinylene carbonate as an acetylene surrogate with a versatile rhodium(III) catalyst. The reaction proceeded at room temperature in biomass derived ethanol solvent. This protocol avoids the use stoichiometric external oxidant, served internal oxidant. C−H/N−H activation annulation manifold broad substrate scope excellent levels regioselectivities. preliminary mechanistic studies suggest facile reversible chelation‐assisted C−H rhodation. Diversification provide access to 4‐substituted isoquinolines, which are complementary previously reported protocols.

Language: Английский

Citations

8

Synthesis of 3‐Methyleneisoindolin‐1‐ones via Rhodium(III)‐Catalyzed C−H/N−H Activation and Annulation of N‐Methoxybenzamides with Potassium Vinyltrifluoroborate DOI Open Access
Vikash Kumar, Parthasarathy Gandeepan

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(22)

Published: Aug. 9, 2024

Abstract Isoindolinones are vital heterocyclic compounds in medicinal chemistry, notable for their diverse bioactivities. Significant attention has been devoted to preparation; however, existing methods unsuitable constructing unsubstituted 3‐methyleneisoindolin‐1‐ones. Herein, we present a rhodium(III)‐catalyzed method synthesizing 3‐methyleneisoindolin‐1‐ones via C−H/N−H activation and annulation of N ‐methoxybenzamides with potassium (ethenyl)trifluoroborate. This approach offers mild reaction conditions, high regioselectivity, efficient yields. Interestingly, sterically demanding or ‐methoxyaromaticamides resulted the formation 2‐vinyl(hetero)aromatic amides instead Mechanistic insights suggest rhodacycle intermediate pathway, highlighting method's potential developing new bioactive isoindolinone derivatives.

Language: Английский

Citations

2

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