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Abstract
The synthesis of vinyl−, aryl−, and hetaryllithiums via tin-lithium exchange is described. The majority of the material in this overview dates from the mid-1980’s to 2006. The primary focus of this overview is the scope of tin-lithium exchange in regards to the range of functionality that can be tolerated in the organostannane precursors.
Highlights
Numerous methods exist for the generation of carbanions in organic synthesis, including reactions of a metal or radical anion metal salt with an organic halide, hydrogen-metal exchange, metal-halogen exchange, and transmetallation
The advantages of this method are the rapidity of the reaction even at low temperatures (−100oC), the absence of potentially reactive byproducts, and the variety of synthetic pathways that exist for the preparation of the required organostannane precursors
This paper presents an overview of recent applications of tin-lithium exchange involving vinyl, aryl- and hetarylstannanes
Summary
Numerous methods exist for the generation of carbanions in organic synthesis, including reactions of a metal or radical anion metal salt with an organic halide, hydrogen-metal exchange, metal-halogen exchange, and transmetallation. An equilibrium is established in which the more stable organolithium compound predominates; reactions of alkyllithiums such as n-BuLi with vinyl- and arylstannanes result in effective tin-lithium exchange. The advantages of this method are the rapidity of the reaction even at low temperatures (−100oC), the absence of potentially reactive byproducts (e.g. alkyl halides in the case of lithium-halogen exchange), and the variety of synthetic pathways that exist for the preparation of the required organostannane precursors. Due to an excellent review of this chemistry covering the literature up through 1984,4 the focus of this overview will be on reports published after this date
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