Rhodium Catalysts Based on Phenyl Substituted Cp Ligands for Indole Synthesis via Oxidative Coupling of Acetanilides and Alkynes

Abstract Rhodium‐catalyzed oxidative coupling of acetanilides and alkynes via C−H activation is the most powerful synthetic tool for producing the indole motif from commercially available precursors. However, this reaction usually requires large catalyst loadings (5 mol% of rhodium). In this study, a 1,2‐diphenylcyclopentadienyl ligand‐based catalyst was developed that works well at 1 mol% loading of rhodium. DFT calculations of the C−H activation step provided insight into its high catalytic activity. The catalyst efficiency was also demonstrated in the synthesis of naturally occurring isocoumarins, such as polygonolide, tubakialactone B and penicimarine F. The developed catalytic protocols tolerate a wide range of functional groups, for example, halide, nitro, hydroxy, and alkoxy.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-08-15
DOI
https://doi.org/10.1002/adsc.202400716
Citations
6
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.50

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article

Rhodium Catalysts Based on Phenyl Substituted Cp Ligands for Indole Synthesis via Oxidative Coupling of Acetanilides and Alkynes

Dmitry A. Loginov, Mger A. Navasardyan, Dmitry V. Muratov, Vladimir B. Kharitonov et al.
6 citations
Advanced Synthesis & Catalysis
Catalytic C–H Functionalization Methods
1.50
article

Rhodium Catalysts Based on Phenyl Substituted Cp Ligands for Indole Synthesis via Oxidative Coupling of Acetanilides and Alkynes

Dmitry A. Loginov, Mger A. Navasardyan, Dmitry V. Muratov, Vladimir B. Kharitonov, Yulia Vladimirovna Nelyubina, А. N. Rodionov, Mikhail S. Nechaev
article en
6 citations

Abstract

Abstract Rhodium‐catalyzed oxidative coupling of acetanilides and alkynes via C−H activation is the most powerful synthetic tool for producing the indole motif from commercially available precursors. However, this reaction usually requires large catalyst loadings (5 mol% of rhodium). In this study, a 1,2‐diphenylcyclopentadienyl ligand‐based catalyst was developed that works well at 1 mol% loading of rhodium. DFT calculations of the C−H activation step provided insight into its high catalytic activity. The catalyst efficiency was also demonstrated in the synthesis of naturally occurring isocoumarins, such as polygonolide, tubakialactone B and penicimarine F. The developed catalytic protocols tolerate a wide range of functional groups, for example, halide, nitro, hydroxy, and alkoxy.

Advanced Synthesis & CatalysisVol. 366(22)
National Research University Higher School of Economics (RU), Russian Academy of Sciences (RU), A. N. Nesmeyanov Institute of Organoelement Compounds (RU), A.V. Topchiev Institute of Petrochemical Synthesis (RU), NS Kurnakova Institute of General and Inorganic Chemistry (RU)
National Research University Higher School of Economics, Ministry of Science and Higher Education of the Russian Federation
Clean water and sanitation
Openalex Percentile: Top 19%
Catalytic C–H Functionalization Methods
1.50
DOIOpen Access PDFOpenAlex
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Rhodium Catalysts Based on Phenyl Substituted Cp Ligands for Indole Synthesis via Oxidative Coupling of Acetanilides and Alkynes — Dmitry A. Loginov, Mger A. Navasardyan, et al. · Advanced Synthesis & Catalysis (2024) | TGRS Research Map | TGRS