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Room temperature, metal-free arylation of aliphatic alcohols.

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.

SUBMITTER: Ghosh R

PROVIDER: S-EPMC4000167 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Room temperature, metal-free arylation of aliphatic alcohols.

Ghosh Raju R Lindstedt Erik E Jalalian Nazli N Olofsson Berit B

ChemistryOpen 20140411 2

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. ...[more]

PMID: 24808991

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