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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Published in | Journal of organometallic chemistry Vol. 964; pp. 122303 - 122309 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
LAUSANNE
Elsevier
15.04.2022
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Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 0022-328X 1872-8561 |
DOI: | 10.1016/j.jorganchem.2022.122303 |