Novel metal-free Lewis acid catalysis by phosphonium salts through hypervalent interaction

Phosphonium salts as a novel metal-free Lewis acid catalyst can be considered as organocatalysts. The introduction of a five-membered dioxaphosphacycle to the phosphonium salt is critical to its function as a Lewis acid catalyst for the Diels-Alder reaction. The key to the successful catalysis by the phosphonium salt is the utilization of hypervalent bonding as a strategic interaction for the generation of an active species. (c) 2005 Elsevier Ltd. All rights reserved.