Metal-free C-H amination of unactivated hydrocarbons with sulfonylimino-λ(3)-bromanes generated in situ from (diacetoxybromo)benzene

Metal-free C-H amination of unactivated hydrocarbons with sulfonylimino-λ(3)-bromanes generated in situ from (diacetoxybromo)benzene

A simple method for direct metal-free C-H amination of unactivated hydrocarbons using easy-handling diacetoxy-λ(3)-bromane and triflylamide or sulfamate esters was developed. The high 2°/3° regioselectivities and deuterium isotope effects suggest a concerted organonitrenoid transition state, analogo...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2015-02, Vol.13 (7), p.2129
Hauptverfasser: Miyamoto, Kazunori, Ota, Taiga, Hoque, Md Mahbubul, Ochiai, Masahito
Format: Artikel
Sprache:eng
Schlagworte:
Amination
Amines - chemical synthesis
Amines - chemistry
Bromobenzenes - chemistry
Hydrocarbons - chemistry
Imines - chemistry
Molecular Structure
Onium Compounds - chemistry
Sulfones - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A simple method for direct metal-free C-H amination of unactivated hydrocarbons using easy-handling diacetoxy-λ(3)-bromane and triflylamide or sulfamate esters was developed. The high 2°/3° regioselectivities and deuterium isotope effects suggest a concerted organonitrenoid transition state, analogous to C-H amination with N-triflylimino-λ(3)-bromane.
ISSN:1477-0539
DOI:10.1039/c4ob02160f