Electrophilic Fluorocyclization of Allyl Silanes

Authors


  • This research was supported by the EPSRC, Syngenta, and the EU (PIEF-GA-2008-220034, MEIF-CT-2006-03970, and MEIF-CT-2004-515589). We thank Dr. Barbara Odell for NMR spectroscopic studies and Dr. Amber L. Thompson of the Oxford Chemical Crystallography Service.

Abstract

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A refreshing cascade: General fluorocyclization reactions will breathe new life into the use of fluorinated hetero- and carbocycles as pharmaceuticals and agrochemicals. Allyl silanes have now been shown to undergo fluorination–cyclization with N[BOND]F reagents to give cis- and trans-substituted fluorinated heterocycles selectively (see scheme). The correct choice of silyl group was critical to prevent competitive fluorodesilylation.

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