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