Hydrothiolation presents an attractive way to transform allenes into allylic thioethers. Herein, we described an efficient visible-light photoredox-promoted nickel-catalyzed hydrothiolation of allenes with functionalized aromatic and aliphatic thiols. This synergistic catalytic system exhibits unprecedentedly high reactivities and regiocontrol for the construction of allylic thioethers, representing the unique synthetic utility of the earth-abundant Ni-catalyzed method compared with the related noble-metal-catalyzed allylation reactions.
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Nickel-Catalyzed Regioselective Hydrothiolation of Allenes Enabled by Visible-Light Photoredox Catalysis.
Org Lett
May 2024
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104 Freiburg im Breisgau, Germany.
Hydrothiolation presents an attractive way to transform allenes into allylic thioethers. Herein, we described an efficient visible-light photoredox-promoted nickel-catalyzed hydrothiolation of allenes with functionalized aromatic and aliphatic thiols. This synergistic catalytic system exhibits unprecedentedly high reactivities and regiocontrol for the construction of allylic thioethers, representing the unique synthetic utility of the earth-abundant Ni-catalyzed method compared with the related noble-metal-catalyzed allylation reactions.
View Article and Find Full Text PDFRhodium-catalyzed regioselective addition of thioacids to terminal allenes: enantioselective access to branched allylic thioesters.
Chem Commun (Camb)
February 2022
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albert Strasse 21, 79104 Freiburg im Breisgau, Germany.
Rhodium-catalyzed regio- and enantioselective hydrothiolation of terminal allenes with thioacids is reported for the atom-economic synthesis of chiral branched allylic thioesters. By using a rhodium(I) catalyst system, diversities of terminal allenes and thioacids afforded the corresponding branched thioesters in excellent regioselectivity, high yield, and good enantioselectivity. This method was also explored for Fmoc-protected aminothioacids for diastereoselective synthesis of the corresponding thioesters.
View Article and Find Full Text PDFZ-Selective Hydrothiolation of Racemic 1,3-Disubstituted Allenes: An Atom-Economic Rhodium-Catalyzed Dynamic Kinetic Resolution.
Angew Chem Int Ed Engl
December 2015
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany).
A Z-selective rhodium-catalyzed hydrothiolation of 1,3-disubstituted allenes and subsequent oxidation towards the corresponding allylic sulfones is described. Using the bidentate 1,4-bis(diphenylphosphino)butane (dppb) ligand, Z/E-selectivities up to >99:1 were obtained. The highly atom-economic desymmetrization reaction tolerates functionalized aromatic and aliphatic thiols.
View Article and Find Full Text PDFAsymmetric rhodium-catalyzed addition of thiols to allenes: synthesis of branched allylic thioethers and sulfones.
Angew Chem Int Ed Engl
March 2015
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany).
A highly regio- and enantioselective hydrothiolation of terminal allenes, a reaction which fulfills the criteria of atom economy, is reported. Applying two chiral rhodium catalyst systems, a wide variety of thiols and allenes could be coupled. Oxidation gave access to the corresponding allylic sulfones in essentially enantiomerically pure form.
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