Zinc-mediated formation of trifluoromethyl ethers from alcohols and hypervalent iodine trifluoromethylation reagents

Raffael Koller; Kyrill Stanek; Daniel Stolz; Raphael Aardoom; Katrin Niedermann; Antonio Togni

doi:10.1002/anie.200900974

Zinc-mediated formation of trifluoromethyl ethers from alcohols and hypervalent iodine trifluoromethylation reagents

Angew Chem Int Ed Engl. 2009;48(24):4332-6. doi: 10.1002/anie.200900974.

Authors

Raffael Koller¹, Kyrill Stanek, Daniel Stolz, Raphael Aardoom, Katrin Niedermann, Antonio Togni

Affiliation

¹ Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich, Switzerland.

PMID: 19434641
DOI: 10.1002/anie.200900974

Abstract

A (fluor)ry of activity: The transfer of an intact trifluoromethyl group from a hypervalent iodine reagent to an aliphatic alcohol occurs smoothly upon activation by zinc bis(triflimide). This constitutes a straightforward method for the preparation of trifluoromethoxy alkyl derivatives, compounds otherwise difficult to access.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Catalysis
Crystallography, X-Ray
Cyclohexanones / chemistry
Ethers / chemical synthesis*
Ethers / chemistry
Fluorine / chemistry*
Iodine / chemistry*
Molecular Conformation
Zinc / chemistry*

Substances

Alcohols
Cyclohexanones
Ethers
triflimide
Fluorine
Iodine
Zinc