Mechanistic Studies on the Catalytic Cycle of Metal Fluoride-Catalyzed Allylation Using Allyltrimethoxysilane in Protic Solvents

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Abstract
The catalytic cycles of CdF2·1-catalyzed and AgF·BINAP-catalyzed allylation using allyltrimethoxysilane in protic solvents were investigated. The experimental and 19F NMR studies strongly supported that metal fluorides were regenerated from silyl fluoride species, and that these reactions were truly fluoride-catalyzed reactions. It was revealed that these catalytic cycles were much different from that of TBAF-catalyzed allylation using allyltrimethylsilane in THF.