Low-Pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes
Dr. Sohajl Movahhed
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
These authors contributed equally to this work.
Search for more papers by this authorJulia Westphal
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
These authors contributed equally to this work.
Search for more papers by this authorDr. Mehmet Dindaroğlu
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
Search for more papers by this authorDr. Anna Falk
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Hans-Günther Schmalz
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
Search for more papers by this authorDr. Sohajl Movahhed
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
These authors contributed equally to this work.
Search for more papers by this authorJulia Westphal
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
These authors contributed equally to this work.
Search for more papers by this authorDr. Mehmet Dindaroğlu
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
Search for more papers by this authorDr. Anna Falk
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Hans-Günther Schmalz
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany
Search for more papers by this authorGraphical Abstract
Combination of a chiral TADDOL-derived phosphine–phosphite ligand with CoCl2 was the key for the development of a robust and reliable protocol for the enantioselective codimerization of various functionalized vinylarenes with ethylene (see scheme).
Abstract
An efficient and practical protocol for the enantioselective cobalt-catalyzed hydrovinylation of vinylarenes with ethylene at low (1.2 bar) pressure has been developed. As precatalysts, stable [L2CoCl2] complexes are employed that are activated in situ with Et2AlCl. A modular chiral TADDOL-derived phosphine–phosphite ligand was identified that allows the conversion of a broad spectrum of substrates, including heterocyclic vinylarenes and vinylferrocene, to smoothly afford the branched products with up to 99 % ee and virtually complete regioselectivity. Even polar functional groups, such as OH, NH2, CN, and CO2R, are tolerated.
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