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- Title
Chalcogenoalkynes: Precursors for the Regioselective Preparation of 2-Chalcogeno-1-halonaphthalenes through [4+2] Cycloaddition.
- Authors
Mantovani, Anderson C.; Back, Davi F.; Zeni, Gilson
- Abstract
Chalcogenoalkynes and o-alkynylbenzaldehydes reacted in the presence of copper(II) salt to give the [4+2] cycloadducts 2-chalcogeno-1-halonaphthalenes in good yields (46-89 %) and high regioselectivities. The methodology was carried out by using CuCl2 or CuCl2/LiBr in 1,2-dichloroethane (DCE) at 80 °C. The potential and generality of this system was evaluated by using a variety of chalcogenoalkynes including aromatic, substituted aromatic, and aliphatic substrates having both sulfur and selenium atoms. In this sequence, due to the ability of the chalcogen atoms to stabilize charges, these substituents exert regiocontrol that guides the selectivity.
- Publication
European Journal of Organic Chemistry, 2012, Vol 2012, Issue 24, p4574
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201200482