Room Temperature, Metal‐Free Arylation of Aliphatic Alcohols

Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal‐free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron‐withdrawing substituents are transferred mos...

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Bibliographic Details
Published in:ChemistryOpen (Weinheim) 2014-04, Vol.3 (2), p.54-57
Main Authors: Ghosh, Raju, Lindstedt, Erik, Jalalian, Nazli, Olofsson, Berit
Format: Article
Language:English
Subjects:
Aliphatic alcohols
alkyl aryl ethers
Aromatic compounds
arylation
Communications
diaryliodonium salts
Ethers
hypervalent iodine
Methodology
Organic Chemistry
organisk kemi
Room temperature
Synthesis
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Summary:Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal‐free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron‐withdrawing substituents are transferred most efficiently, and unsymmetric iodonium salts give chemoselective arylations. The methodology has been applied to the formal synthesis of butoxycaine. Easy, quick and green! Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under mild and metal‐free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields.
ISSN:2191-1363
2191-1363
DOI:10.1002/open.201402006