Palladium‐Catalyzed Regioselective C(4)−H Fluoroalkoxylation of Indoles through Weak Chelation Assistance DOI

Muniyappa Vijaykumar,

Rajesh G. Gonnade, Benudhar Punji

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Abstract Installing fluoroalkyl motifs into biorelevant indoles is particularly interesting due to their ubiquitous presence in drug molecules. Herein, we demonstrate the regioselective C4 fluoroalkoxylation of using fluoroalcohols via palladium‐catalyzed chelation‐assisted C─H activation. The weak chelating benzoyl moiety at C3 position acts as a directing group for remote C(4)─H diversely substituted indoles. This methodology demonstrates high level regioselectivity and tolerates range crucial functional groups, yielding diverse trifluoroalkoxylated moderate good yields. Removal directing/protecting groups further functionalization established synthetic utility methodology. A preliminary mechanistic investigation conducted by isolating palladacycle intermediate performing deuterium scrambling study.

Language: Английский

Recent advances in catalytic approaches for the synthesis of 3-substituted indoles: mechanisms and strategies DOI Creative Commons
Ebraheem Abdu Musad Saleh,

Kakul Hussin Firoz,

Subasini Uthirapathy

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(16), P. 12255 - 12290

Published: Jan. 1, 2025

This review highlights recent advancements in the catalytic synthesis of 3-substituted indoles, focusing on improved efficiency, selectivity, and sustainability attained through use various systems green chemistry approaches.

Language: Английский

Citations

0
Electrochemical synthesis of biomass-derived aromatic N-heterocycles by using Ni-based hierarchical nanosheets catalysts DOI
Zhengxue Quan,

Wanling Xu,

Jinzhu Chen

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 116218 - 116218

Published: May 1, 2025

Language: Английский

Citations

0
A Catalytic Version of the Knorr Pyrrole Synthesis Permits Access to Pyrroles and Pyridines DOI

Max Leinert,

Τ. Irrgang, Rhett Kempe

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(46), P. 32098 - 32104

Published: Nov. 11, 2024

Aromatic N-heterocycles, such as pyrroles and pyridines, are important natural products bulk fine chemicals with numerous applications active ingredients of pharmaceuticals agrochemicals, catalysts, in materials sciences. We report here a catalytic version the Knorr pyrrole synthesis which simple diversely available starting materials, 1,2-amino alcohols or 1,3-amino keto esters, undergo dehydrogenative coupling to form respectively. Our reaction forms hydrogen collectible (and usable) byproduct is mediated by well-defined Mn catalyst. The highly functionalized heterocycles was demonstrated, 35 compounds, not yet reported literature, were introduced.

Language: Английский

Citations

2
Palladium‐Catalyzed Regioselective C(4)−H Fluoroalkoxylation of Indoles through Weak Chelation Assistance DOI

Muniyappa Vijaykumar,

Rajesh G. Gonnade, Benudhar Punji

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Abstract Installing fluoroalkyl motifs into biorelevant indoles is particularly interesting due to their ubiquitous presence in drug molecules. Herein, we demonstrate the regioselective C4 fluoroalkoxylation of using fluoroalcohols via palladium‐catalyzed chelation‐assisted C─H activation. The weak chelating benzoyl moiety at C3 position acts as a directing group for remote C(4)─H diversely substituted indoles. This methodology demonstrates high level regioselectivity and tolerates range crucial functional groups, yielding diverse trifluoroalkoxylated moderate good yields. Removal directing/protecting groups further functionalization established synthetic utility methodology. A preliminary mechanistic investigation conducted by isolating palladacycle intermediate performing deuterium scrambling study.

Language: Английский

Citations

1