Trifluoromethyl sulfoxides from allylic alcohols and electrophilic SCF3 donor by [2,3]-sigmatropic rearrangement

Mayaka Maeno; Norio Shibata; Dominique Cahard

doi:10.1021/acs.orglett.5b00750

Trifluoromethyl sulfoxides from allylic alcohols and electrophilic SCF3 donor by [2,3]-sigmatropic rearrangement

Org Lett. 2015 Apr 17;17(8):1990-3. doi: 10.1021/acs.orglett.5b00750. Epub 2015 Apr 1.

Authors

Mayaka Maeno^{1

2}, Norio Shibata², Dominique Cahard¹

Affiliations

¹ †UMR 6014 CNRS C.O.B.R.A., Université de Rouen, INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint Aignan, France.
² ‡Department of Nanopharmaceutical Science, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

PMID: 25831154
DOI: 10.1021/acs.orglett.5b00750

Abstract

An electrophilic trifluoromethylthiolation of allylic alcohols produces the corresponding allylic trifluoromethanesulfenates, which spontaneously rearrange into trifluoromethyl sulfoxides via a [2,3]-sigmatropic rearrangement. The reaction is straightforward and proceeds in good to high yields for the preparation of various allylic trifluoromethyl sulfoxides.

Publication types

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

MeSH terms

Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Molecular Structure
Propanols / chemistry*
Sulfoxides / chemical synthesis*
Sulfoxides / chemistry

Substances

Hydrocarbons, Fluorinated
Propanols
Sulfoxides
allyl alcohol