A Straightforward Procedure for the [2+2+2] Cycloaddition of Enediynes

Enediynes undergo intramolecular [2+2+2] cycloaddition in the presence of cobalt(II) iodide (CoI2), manganese and an N‐heterocyclic carbene (IPr) generated in situ from the corresponding imidazolium salt and butyllithium (BuLi). Polycyclic cyclohexadienes are obtained selectively. This new method re...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-01, Vol.351 (1-2), p.271-275
Main Authors: Geny, Anaïs, Gaudrel, Sophie, Slowinski, Franck, Amatore, Muriel, Chouraqui, Gaëlle, Malacria, Max, Aubert, Corinne, Gandon, Vincent
Format: Article
Language:English
Subjects:
cobalt
cycloaddition
dienes
manganese
N-heterocyclic carbenes
polycycles
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Summary:Enediynes undergo intramolecular [2+2+2] cycloaddition in the presence of cobalt(II) iodide (CoI2), manganese and an N‐heterocyclic carbene (IPr) generated in situ from the corresponding imidazolium salt and butyllithium (BuLi). Polycyclic cyclohexadienes are obtained selectively. This new method represents an interesting alternative to those employing air‐sensitive cyclopentadienylcobalt [CpCoL2 (L=CO, C2H4)] catalysts. Moreover, the N‐heterocyclic carbene can be used catalytically, which is a significant improvement compared to the corresponding phosphine‐based system which requires an excess of ligand.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800646