Synthesis 2006(21): 3589-3596  
DOI: 10.1055/s-2006-942512
PAPER
© Georg Thieme Verlag Stuttgart · New York

Rhodium- or Copper-Catalysed CH-Insertion of Carbenoids into Dihydro­aromatic Compounds and Acyclic 1,4-Dienes

Gerhard Hilt*, Fabrizio Galbiati
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein Straße, 35043 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: Hilt@chemie.uni-marburg.de;
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Publikationsverlauf

Received 6 April 2006
Publikationsdatum:
25. Juli 2006 (eFirst)

Abstract

A straightforward reaction sequence consisting of a cobalt-catalysed Diels-Alder reaction for the generation of dihydro­aromatic compounds and a rhodium- or alternatively a copper-catalysed CH-insertion reaction of carbenoids from diazo esters generates highly substituted benzene derivatives. When acyclic 1,4-dienes are synthesised by a cobalt-catalysed 1,4-hydrovinylation reaction, the rhodium-catalysed conversion with diazo esters leads to cyclopropanation rather than CH-insertion products.

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Hilt, G.; Galbiati, F. Org. Lett. 2006, 8, 2195