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

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‐dip...

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Bibliographic Details
Published in:	Advanced synthesis & catalysis Vol. 366; no. 22; pp. 4729 - 4736
Main Authors:	Kharitonov, Vladimir B., Muratov, Dmitry V., Rodionov, Alexey N., Nelyubina, Yulia V., Navasardyan, Mher A., Nechaev, Mikhail S., Loginov, Dmitry A.
Format:	Journal Article
Language:	English
Published:	Heidelberg Wiley Subscription Services, Inc 19-11-2024
Subjects:	Acetanilide Alkynes Annulation Catalysts Catalytic activity Chemical synthesis Coupling C−H activation Functional groups Homogeneous catalysis Indoles Isocoumarins Ligands Rhodium
Online Access:	Get full text
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Summary:	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.
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.202400716