Ferrocene catalyzed carbohydroxylation of alkenes using H2O and cycloketone oxime esters

A cyanoalkyl-hydroxylation reaction of aryl alkenes has been successfully devised, employing ferrocene as a catalyst for the addition of a cycloketone oxime ester and H2O across the double bond of the alkene. This environmentally friendly approach employs a solvent mixture consisting of water and de...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-11, Vol.21 (42), p.8482-8487
Hauptverfasser: Ajmeera, Sriram, Golagani, Durga, Srirama Murthy Akondi
Format: Artikel
Sprache:eng
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Zusammenfassung:A cyanoalkyl-hydroxylation reaction of aryl alkenes has been successfully devised, employing ferrocene as a catalyst for the addition of a cycloketone oxime ester and H2O across the double bond of the alkene. This environmentally friendly approach employs a solvent mixture consisting of water and demonstrates redox neutrality, along with exceptional regio- and chemoselectivity, leading to the formation of diverse distal hydroxy-nitrile compounds. Moreover, this research presents noteworthy contributions in terms of late-stage functionalization of complex molecules and offers valuable insights into the mechanistic aspects of the reaction.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01481a