Letter

Amidinate Salt of Hexafluoroacetone Hydrate for the Preparation of Fluorinated Compounds by the Release of Trifluoroacetate

Department of Medicinal Chemistry and Molecular Pharmacology and Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States
Org. Lett., 2013, 15 (1), pp 208–211
DOI: 10.1021/ol303291x
Publication Date (Web): December 14, 2012
Copyright © 2012 American Chemical Society
dcolby@purdue.edu, †

Department of Medicinal Chemistry and Molecular Pharmacology.

, ‡

Department of Chemistry.

Abstract

Abstract Image

A powerful, new reagent, an amidinate salt of hexafluoroacetone hydrate, is an air-stable salt that can be used for the preparation of fluorinated organic molecules. Nucleophilic trifluoromethylation reactions are demonstrated following the base-promoted release of trifluoroacetate. This reagent is soluble in many polar organic solvents and produces fluoroform, following the release of trifluoroacetate. Reactions with this reagent and common electrophiles provide excellent yields of trifluoromethylated products.

Supporting Information


Full experimental details, spectroscopic data, and X-ray data. This material is available free of charge via the Internet at http://pubs.acs.org.

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

Metrics

Article Views: 3,330 Times
Received 30 November 2012
Published online 14 December 2012
Published in print 4 January 2013
Learn more about these metrics Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.
+
More Article Metrics
Explore by: