Iron-Catalyzed Arylation of Aromatic Ketones and Aldehydes Mediated by Organosilanes

A simple and efficient iron‐catalyzed method for arylation of aromatic carbonyl compounds is reported. The use of 4 % FeCl3 or Fe(acac)3 as the catalyst, in combination with a slight excess of chlorotrimethylsilane and triethylsilane, chlorination of benzylic ketones and aldehydes with subsequent Fr...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2014-07, Vol.2014 (19), p.4137-4147
Main Authors: Savela, Risto, Majewski, Marcin, Leino, Reko
Format: Article
Language:English
Subjects:
Aldehydes
Homogeneous catalysis
Iron
Silanes
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:A simple and efficient iron‐catalyzed method for arylation of aromatic carbonyl compounds is reported. The use of 4 % FeCl3 or Fe(acac)3 as the catalyst, in combination with a slight excess of chlorotrimethylsilane and triethylsilane, chlorination of benzylic ketones and aldehydes with subsequent Friedel–Crafts alkylation of arenes is achieved. Although the method is limited by the general constraints associated with Friedel–Crafts alkylation reactions, robust applications for the synthesis of pharmaceutical intermediates and so on can be envisioned. A robust one‐pot, iron‐catalyzed chlorination Friedel–Crafts alkylation reaction of benzylic carbonyl compounds, mediated by chlorotrimethylsilane and triethylsilane, has been developed to yield substituted diaryl and triaryl building blocks.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402023