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Synthesis 2014; 46(15): 2040-2044
DOI: 10.1055/s-0034-1378375
DOI: 10.1055/s-0034-1378375
practical synthetic procedures
Cobalt-Catalysed Transformations of 1,3,5-Hexatrienes on a Large Scale
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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