Abstract
A silver-catalyzed three-component reaction involving alkynes, Selectfluor®, and diethyl phosphite was employed for the one-pot formation of C(sp2)–F and C(sp2)–P bonds to provide an efficient access to β-fluorovinylphosphonates in a highly regio- and stereoselective manner under mild reaction conditions. This reaction is operationally simple and offers an excellent functional group tolerance as well as a broad substrate scope that includes both terminal and internal alkynes. The reaction proceeded through the oxidative generation of a P-centered radical and subsequent fluorine atom transfer.
Highlights
As one of the most important topics in organic chemistry, the introduction of fluorine and phosphorus atoms into double bonds is an attractive approach for the synthesis of a variety of valuable organic compounds [1,2,3,4,5,6,7]
We investigated the reaction of phenylacetylene (1a), Selectfluor®, and diethyl phosphite to afford β-fluorovinylphosphonates under mild conditions
Substrate scope and excellent functional group tolerance, this simple protocol may represent a general, one-step approach for the preparation of β-fluorophosphonate frameworks for the use in medicinal chemistry
Summary
As one of the most important topics in organic chemistry, the introduction of fluorine and phosphorus atoms into double bonds is an attractive approach for the synthesis of a variety of valuable organic compounds [1,2,3,4,5,6,7]. Well-established transition metal-catalyzed radical difunctionalization of unsaturated carbon–carbon bonds, the work of Li’s group and others concerning the silver-catalyzed phosphonofluorination of alkenes [24,25,26], we present a general silver-catalyzed regio- and stereoselective phosphonofluorination of alkynes using Selectfluor® and phosphonates as reactants (Scheme 1). We investigated the reaction of phenylacetylene (1a), Selectfluor®, and diethyl phosphite to afford β-fluorovinylphosphonates under mild conditions.
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