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 [in Japanese] Simplification of an Organic Synthetic Process Based on a Light-fluorous Strategy [in Japanese]
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Organic molecules bearing small fluorous tags (C<SUB>6</SUB>F<SUB>13</SUB>, C<SUB>8</SUB>F<SUB>17</SUB>) 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.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 66(7), 694-704, 2008-07-01
The Society of Synthetic Organic Chemistry, Japan