Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 17, Pages 3425-3436Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300746
Keywords
aromatic enynes; cycloisomerization; gold; palladium; regioselectivity
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Funding
- CNRS
- ANR [ANR-10-LABX-33]
- Lebanese University
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Aromatic enynes can be transformed into arylnaphthalenes or benzofulvenes depending on the reaction conditions. Under gold(I) catalysis, exclusive or major 6-endo-dig cyclization took place leading to arylnaphthalenes. However, a catalytic system based on palladium iodide/1,3-bis(diphenylphosphino)propane, in the presence of cesium carbonate as a base was necessary to furnish exclusively 5-exo-dig cyclization pattern, regardless of the electronic effects of the substituents. In the latter transformation, a mechanistic study (kinetic isotopic effect, density functional theory) involving a CH activation is suggested for the exclusive formation of benzofulvenes.
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