January 3, 2018 Journal article Open Access

Guojiao Wu and Axel Jacobi von Wangelin

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  <identifier identifierType="DOI">10.25592/uhhfdm.684</identifier>
  <creators>
    <creator>
      <creatorName>Guojiao Wu and Axel Jacobi von Wangelin</creatorName>
    </creator>
  </creators>
  <titles>
    <title>Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes</title>
  </titles>
  <publisher>Universität Hamburg</publisher>
  <publicationYear>2018</publicationYear>
  <dates>
    <date dateType="Issued">2018-01-03</date>
  </dates>
  <language>en</language>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://www.fdr.uni-hamburg.de/record/684</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsPartOf">10.25592/uhhfdm.683</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="https://creativecommons.org/licenses/by/4.0/legalcode">Creative Commons Attribution 4.0 International</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">&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;</description>
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