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Synthesis 2021; 53(22): 4297-4307
DOI: 10.1055/s-0037-1610774
DOI: 10.1055/s-0037-1610774
special topic
Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award
Simple Synthesis of Fluorinated Ene-Ynes via In Situ Generation of Allenes
Funding was provided by UCLA, the National Science Foundation Major Research Instrumentation Program (NSF MRI; CHE-1048804), the Alfred P. Sloan Foundation (FG-2018-10855 to E.M.S.) and the NSF (GRFP 2018270309 to J.A.J.).
Abstract
Fluorination of small molecules is a key route toward modulating reactivity and bioactivity. The 1,3 ene-yne functionality is an important synthon towards complex products, as well as a common functionality in biologically active molecules. Here, we present a new synthetic route towards fluorinated ene-ynes from simple starting materials. We employ gas chromatography-mass spectrometry analysis to probe the sequential eliminations necessary for this transformation and observe an allene intermediate. The ene-yne products are sufficiently fluorous to enable purification via fluorous extraction. This methodology will allow facile access to functional, fluorous ene-ynes.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610774.
- Supporting Information
Publication History
Received: 18 March 2021
Accepted after revision: 27 April 2021
Article published online:
16 June 2021
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