Ligand Control of the Cobalt-Catalysed 1,4-Hydrovinylation Reaction

Marion Arndt; Mehmet Dindaroğlu; Hans-Günther Schmalz; Gerhard Hilt

doi:10.1055/s-0032-1316796

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(22): 3534-3542
DOI: 10.1055/s-0032-1316796

paper

Ligand Control of the Cobalt-Catalysed 1,4-Hydrovinylation Reaction

Authors

Marion Arndt

^aFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany eMail: Hilt@chemie.uni-marburg.de Fax: +49(6421)2825677
Mehmet Dindaroğlu

^bDepartment für Chemie, Universität zu Köln, Greinstr. 4, 50939 Cologne, Germany
Hans-Günther Schmalz

^bDepartment für Chemie, Universität zu Köln, Greinstr. 4, 50939 Cologne, Germany
Gerhard Hilt*

^aFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany eMail: Hilt@chemie.uni-marburg.de Fax: +49(6421)2825677

Abstract

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Abstract

The application of cobalt catalysts to the hydrovinylation of unsymmetrical alkenes and 1,3-dienes was investigated using modular phosphine-phosphite ligands to evaluate the influence of the ligands on the regioselectivity of the reaction. While a ligand with a TADDOL subunit (SchmalzPhos) gave the best results for the β-4 regioisomer, the corresponding BINOL-derived ligand gave predominantly the β-1 regioisomer. The application of (E)-2-methylpenta-1,3-diene in combination with the (nonracemic) BINOL-derived ligand generated the β-4 regioisomer in excellent yields and very high regioselectivities for a number of terminal alkenes bearing various functional groups. In one case, the enantiomeric excess of a chiral product, i.e. a 3,5-dimethylhexa-1,4-diene derivative, was determined by chiral RP-HPLC to be 78% ee.

Key words

alkene - catalysis - cobalt - diene - 1,4-hydrovinylation

Volltext

Referenzen

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