Journal article Open Access

Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes

Guojiao Wu and Axel Jacobi von Wangelin


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    <subfield code="a">&lt;p&gt;Stereoselective additions of highly functionalized reagents to available unsaturated hydrocarbons are an&lt;br&gt;
attractive synthetic tool due to their high atom economy, modularity, and rapid generation of&lt;br&gt;
complexity. We report efficient cobalt-catalyzed (E)-halofluoroalkylations of alkynes/alkenes that enable&lt;br&gt;
the construction of densely functionalized, stereodefined fluorinated hydrocarbons. The mild conditions&lt;br&gt;
(2 mol% cat., 20 C, acetone/water, 3 h) tolerate various functional groups, i.e. halides, alcohols,&lt;br&gt;
aldehydes, nitriles, esters, and heteroarenes. This reaction is the first example of a highly stereoselective&lt;br&gt;
cobalt-catalyzed halo-fluoroalkylation. Unlike related cobalt-catalyzed reductive couplings and Hecktype&lt;br&gt;
reactions, it operates via a radical chain mechanism involving terminal halogen atom transfer which&lt;br&gt;
obviates the need for a stoichiometric sacrificial reductant.&lt;/p&gt;</subfield>
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