Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones

We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-07, Vol.359 (13), p.2222-2228
Main Authors: Zhao, Zhensheng, Kulkarni, Kaivalya G., Murphy, Graham K.
Format: Article
Language:English
Subjects:
Benzaldehyde
Chemical synthesis
Chlorine
diazo compounds
Fluorine
halogenation
Hydrazones
hypervalent compounds
Iodine
Reagents
synthetic methods
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction between iodane and hydrazone. This is the first use of non‐α‐stabilized diazo compounds in this reaction, which provided an efficient synthesis of aryldifluoromethane (ArCHF2) and aryldichloromethane (ArCHCl2) derivatives.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700393