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. 2014 Apr;3(2):54-7.
doi: 10.1002/open.201402006. Epub 2014 Apr 11.

Room temperature, metal-free arylation of aliphatic alcohols

Raju Ghosh  1 , Erik Lindstedt  1 , Nazli Jalalian  1 , Berit Olofsson  1
Affiliations

Room temperature, metal-free arylation of aliphatic alcohols

Raju Ghosh et al. ChemistryOpen. 2014 Apr.

Abstract

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.

Keywords: aliphatic alcohols; alkyl aryl ethers; arylation; diaryliodonium salts; hypervalent iodine.

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Figures

Figure 1
Figure 1
Synthesis of alkyl aryl ethers.
Scheme 1
Scheme 1
Phenylation of aliphatic alcohols. [a] At 40 °C.
Scheme 2
Scheme 2
Chemoselectivity aspects and arylation scope. [a] NaH was used. [b] At 40 °C. [c] No alcohol was added.
Scheme 3
Scheme 3
Formal synthesis of butoxycaine.
See this image and copyright information in PMC

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