Synthesis 2006(1): 182-185  
DOI: 10.1055/s-2005-921747
PSP
© Georg Thieme Verlag Stuttgart · New York

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

Marc Gingras*, Yoann M. Chabre, J.-M. Raimundo
Chemical Laboratory of Organic and Metallic Materials, Faculty of Sciences, University of Nice-Sophia Antipolis, 28 Av. Valrose, 06108 Nice Cedex 2, France
Fax: +33(4)92076578; e-Mail: [email protected];
Further Information

Publication History

Received 17 May 2005
Publication Date:
16 December 2005 (online)

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.

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