Abstract
A LiCl-mediated and palladium(II)-catalyzed oxidative cyclization of furan-ynes via dearomatizing alkoxyalkenylation of furan is reported to afford polyfunctionalized spiro-dihydrofurans with diastereospecification and high Z/E selectivity. This protocol is likely to involve chloropalladation of alkynes, subsequent intramolecular dearomatizing alkenylation of furan, and final O-allylation. The density functional theory (DFT) calculations demonstrated that the coordination of furan with dissolved Li+ weakens its nucleophilicity and promoted the Heck insertion, and dissolved Cl- promoted chloropalladation of alkynes.
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