Volume 22, Issue 22 p. 7381-7384
Communication

Low-Pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes

Dr. Sohajl Movahhed

Dr. Sohajl Movahhed

Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany

These authors contributed equally to this work.

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Julia Westphal

Julia Westphal

Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany

These authors contributed equally to this work.

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Dr. Mehmet Dindaroğlu

Dr. Mehmet Dindaroğlu

Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany

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Dr. Anna Falk

Dr. Anna Falk

Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany

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Prof. Dr. Hans-Günther Schmalz

Corresponding Author

Prof. Dr. Hans-Günther Schmalz

Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Cologne, Germany

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First published: 21 March 2016
Citations: 31

Graphical 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.