ライトフルオラスタグを基点とする有機反応プロセスの簡略化

Abstract

Organic molecules bearing small fluorous tags (C6F13, C8F17) are called light fluorous molecules. Light fluorous reagents, scavengers and catalysts are especially convenient since they typically induce reactions of organic substrates under the same conditions as their non-fluorous relatives, but are reliably removed from crude reaction products by fluorous solid phase extraction. Herein we report light fluorous versions of Grubbs-Hoveyda metathesis catalysts, Mukaiyama reagent, and Fmoc reagent. These exhibit the expected reactivity profile, are readily recovered from reaction mixtures by fluorous solid phase extraction. In addition, we describe reverse-fluorous solid phase extraction. In a reversal of the roles of solid and liquid phases in standard fluorous solid phase extraction, a mixture is charged to a polar solid phase (standard silica gel) and then eluted with a fluorous solvent. The organic components of the mixture are retained, while the fluorous components pass.