Iron-Catalyzed Intermolecular Oxyamination of Terminal Alkenes Promoted by HFIP Using Hydroxylamine Derivatives

An atom-economical intermolecular iron-catalyzed oxyamination of alkenes is described herein. The insertion of oxygenated and nitrogenated moieties from the hydroxylamine substrate was observed with full regio- and chemo-selectivity for terminal alkenes in good yields. HFIP as a solvent appeared to...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 7; pp. 4720 - 4729
Main Authors Kirby, Georgina, Prestat, Guillaume, Berhal, Farouk
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.04.2023
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXYAMIDATION
DIFUNCTIONALIZATION
STYRENES
INTRAMOLECULAR AMINOHYDROXYLATION
SHARPLESS ASYMMETRIC AMINOHYDROXYLATION
AMINO
AMINOACETOXYLATION
OLEFINS
METAL-FREE
AMINOOXYGENATION
catalysis
Nitrene
Hydroxylamine
Iron
Oxyamination
Online AccessGet full text

Cover

More Information
Summary:An atom-economical intermolecular iron-catalyzed oxyamination of alkenes is described herein. The insertion of oxygenated and nitrogenated moieties from the hydroxylamine substrate was observed with full regio- and chemo-selectivity for terminal alkenes in good yields. HFIP as a solvent appeared to have a synergistic effect with the iron catalyst to promote the formation of the oxyaminated products. Preliminary mechanistic studies suggest a pathway going through an aziridination reaction followed by an in situ ring opening.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00198