Journal of Organic Chemistry p. 3595 - 3611 (2019)
Update date:2022-08-11
Topics:
Purin?, Mikus
Mishnev, Anatoly
Turks, Maris
A general method for generation of allyl carbenium ions from propargyl silanes via a 1,2-silyl shift by Br?nsted acids is reported. Two possible reaction pathways are described. Deprotonation results in silyl dienes with yields from 52% to 92%. Intramolecular Friedel-Crafts reactions of aryl-substituted systems give access to silyl indenes with yields of 18-90% depending on the substitution pattern. The obtained products have been shown to react as alkenyl silanes in Hiyama coupling and electrophilic substitution and as dienes in Diels-Alder cycloaddition.
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