Late-stage deoxyfluorination of alcohols with PhenoFluor

Filippo Sladojevich; Sophie I Arlow; Pingping Tang; Tobias Ritter

doi:10.1021/ja3125405

Late-stage deoxyfluorination of alcohols with PhenoFluor

J Am Chem Soc. 2013 Feb 20;135(7):2470-3. doi: 10.1021/ja3125405. Epub 2013 Feb 11.

Authors

Filippo Sladojevich¹, Sophie I Arlow, Pingping Tang, Tobias Ritter

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.

Abstract

An operationally simple protocol for the selective deoxyfluorination of structurally complex alcohols is presented. Several fluorinated derivatives of natural products and pharmaceuticals have been prepared to showcase the potential of the method for late-stage diversification and its functional group compatibility. A series of simple guidelines for predicting the selectivity in substrates with multiple alcohols is given.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Binding Sites
Halogenation
Imidazolines / chemistry*
Molecular Structure

Substances

Alcohols
Imidazolines
PhenoFluor

Abstract

Publication types

MeSH terms

Substances

Grants and funding