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Synthesis 2006(21): 3589-3596
DOI: 10.1055/s-2006-942512
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
Further Information
Publication History
Received
6 April 2006
Publication Date:
25 July 2006 (online)


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.
Key words
catalysis - cobalt - copper - cyclopropanation - 1,4-diene