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. 2015 May 4;54(19):5662-5.
doi: 10.1002/anie.201500902. Epub 2015 Mar 20.

Alkyl Aryl Ether Bond Formation with PhenoFluor

Xiao Shen  1 , Constanze N Neumann, Claudia Kleinlein, Nathaniel W Goldberg, Tobias Ritter
Affiliations

Alkyl Aryl Ether Bond Formation with PhenoFluor

Xiao Shen et al. Angew Chem Int Ed Engl. .

Abstract

An alkyl aryl ether bond formation reaction between phenols and primary and secondary alcohols with PhenoFluor has been developed. The reaction features a broad substrate scope and tolerates many functional groups, and substrates that are challenging for more conventional ether bond forming processes may be coupled. A preliminary mechanistic study indicates reactivity distinct from conventional ether bond formation.

Keywords: CO bond formation; Mitsunobu reaction; PhenoFluor; alkyl aryl ethers; fluorine.

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Figures

Scheme 1
Scheme 1
Fluorination and etherification reactions with PhenoFluor. Boc = tert-butyloxycarbonyl, TMS = trimethylsilyl.
Scheme 2
Scheme 2
Diaryl ether formation.
Scheme 3
Scheme 3
The 18O label originates from phenol.
Scheme 4
Scheme 4
Proposed mechanism. Ar=2,6-diisopropylphenyl.
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