FLUOROUS NUCLEOPHILIC SUBSTITUTION OF ALCOHOLS AND REAGENTS FOR USE THEREIN

摘要

A method of effecting a nucleophilic substitution of an alcohol to produce a target product includes the steps of: reacting the alcohol and a nucleophile with an azodicarboxylate and a phosphine. At least one of the azodicarboxylate and the phosphine includes at least one fluorous tag. In several embodiments, the azodicarboxylate includes at least one fluorous tag, and the phosphine includes at least one fluorous tag. A compound has the formula: In the above formula n1, n2, n3, n4, n5, n6, n7, n8, n9 and n10 are independently 1 or =. X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19 and X20 are independently H, F, C1,an alkyl group, an aryl group or an alkoxy group. R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 and R16 are independently H, F, C1, an alkyl group, an alkoxy group, a thioalkyl group, a dialkylamino group, a nitro group, a fluorinated amine group, O-Rf1, S-Rf2, or N(Rf3)(R22), Wherein R22 is an alkyl group or Rf4, and wherein Rf1, Rf2, Rf3 and Rf4 are independently a fluorous group selected from the group of a perfluoroalkyl group, a hydrofluoroalkyl group, a fluorinated ether group or a fluorinated amine group. At least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 or R16 is O-Rf1, -N(Rf3)(R22), a perfluoroalkyl group, a hydrofluoroalkyl group, a fluorinated ether group or a fluorinated amine group.