Tetrabutylammonium Difluorotriphenylstannate [Bu ₄ N][Ph ₃ SnF ₂ ]: Delivering­ Carbon or Fluorine Ligands via Hypercoordination

Abstract

The reagent, tetrabutylammonium difluorotriphenylstannate, was easily prepared on a multigram scale (∼100 g). Several of its applications are presented, either as a soluble, thermally stable and anhydrous nucleophilic fluorinating agent or as a synthetic equivalent to PhMgX or PhLi species under aqueous and aerobic conditions. The proposed methodologies emphasize the concept of hypercoordination and its usefulness for improving selectivity, reactivity and shelf-stability of reagents.

Key words

fluorination - tin - carbanions - sulfur - hypercoordination

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