Directing group enabled 'On-Water' C-H bond functionalization of ferrocene derivatives

Herein, we report an 'on-water' methodology for the selective synthesis of bis C -H bond functionalized ferrocene derivatives under relatively mild reaction conditions. In this work, 8-aminoquinoline and picolinamide were used as selective, inexpensive, and easily removable bidentate direc...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 964; pp. 122303 - 122309
Main Authors Verma, Ashutosh, Dolui, Pritam, Hazra, Susanta, Elias, Anil J. J.
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier 15.04.2022
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
ACTIVATION
Bis C-H bond functionalization
Bidentate-directing groups
ARYLATION
REACTIVITY
reusability
Greener pathway
8-AMINOQUINOLINE
METAL SANDWICH COMPOUNDS
On-water reaction
Ferrocene
ALCOHOLS
CHEMISTRY
MICELLAR CATALYSIS
COUPLINGS
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Summary:Herein, we report an 'on-water' methodology for the selective synthesis of bis C -H bond functionalized ferrocene derivatives under relatively mild reaction conditions. In this work, 8-aminoquinoline and picolinamide were used as selective, inexpensive, and easily removable bidentate directing groups on ferrocene and the reactions were performed exclusively in water. Reaction of ferrocene 8-aminoquinoline carboxamide with various aryl/alkyl iodides using 5 mol% of Pd(OAc)(2) and water as the solvent resulted in 61- 93% isolated yield of the cyclopentadienyl bis-arylated products. Similarly, using ferrocene-picolinamide as the substrate with aryl iodides, 55-98% yield of the cyclopentadienyl substituted ferrocene derivatives were obtained. The heterogeneity and stability of substrates, catalyst, and products under 'on-water' reaction conditions enabled us to explore the solvent, i.e., water and the catalyst's reusability. Control experiments confirm the in situ formation of palladacycles during the reaction. (C) 2022 Elsevier B.V. All rights reserved.
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2022.122303