Synthesis 2014; 46(15): 2040-2044
DOI: 10.1055/s-0034-1378375
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalysed Transformations of 1,3,5-Hexatrienes on a Large Scale

Anastasia Schmidt
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany   Fax: +49(6421)2825677   Email: [email protected]
,
Elias Maiterth
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany   Fax: +49(6421)2825677   Email: [email protected]
,
Gerhard Hilt*
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany   Fax: +49(6421)2825677   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 22 May 2014

Accepted after revision: 12 June 2014

Publication Date:
09 July 2014 (online)


Abstract

The cobalt-catalysed 1,4-hydrovinylation of an aryl-substituted 1,3,5-hexatriene was investigated on a large scale for the synthesis of a double-skipped 1,4,7-triene product. The reaction proceeds via a regioselective C–H activation of the alkene and the exclusive formation of the 4Z-double bond. The cobalt-catalysed 1,4-hexatrienylation of a butadiene derivative led exclusively to the desired all-E tetraene product. Finally, the cobalt-catalysed Diels–Alder reaction with trimethylsilyl-substituted alkynes was investigated. The cycloadducts were generated with excellent chemo- and regioselectivity to give the corresponding stilbene derivative.

 
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