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Gaining absolute control of the regiochemistry in the cobalt-catalyzed 1,4-hydrovinylation reaction.

Organic letters (2011-11-02)
Marion Arndt, Mehmet Dindaroğlu, Hans-Günther Schmalz, Gerhard Hilt
ABSTRACT

The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates the corresponding linear product in both excellent yields and regioselectivities. The catalyst system exhibits a high tolerance toward functional groups, and the very mild reaction conditions allow the synthesis of 1,4-dienes without isomerization into conjugated systems.

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Sigma-Aldrich
Allylboronic acid pinacol ester, 97%