Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 25, Pages 8751-8757Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0488098
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First generation fluorous DEAD reagent bis(perfluorohexylethyl)azo dicarboxylate (C6F13(CH2)(2)O2CN=NCO2(CH2)(2)C6F13, F-DEAD-1) has been shown to underperform relative to diisopropylazodicarboxylate in difficult Mitsunobu reactions involving hindered alcohols or less acidic pronucleophiles (phenols). Two new second generation fluorous reagents bearing propylene spacers instead of the ethylene spacers show expanded reaction scope while retaining the easy fluorous separation features. Byproducts from half fluorous reagent perfluorooctylpropyl tert-butyl azo dicarboxylate (C8F17(CH2)(3)O2CN=(NCO2Bu)-Bu-t, F-DEAD-2) can be removed by fluorous flash chromatography, and byproducts from bis(perfluorohexylpropyl)azo dicarboxylate (C6F13(CH2)(3)O2CN=NCO2(CH2)(3)C6F13, F-DEAD-3) can be removed by fluorous solid-phase extraction. The new reagents promise to provide general and complementary solutions for separation problems in Mitsunobu reactions without restricting reaction scope.
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