Fluorous Mitsunobu reagents and reactions

被引：94

作者：

Dandapani, S ^{[1
]}

Curran, DP ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 20期

基金：

美国国家卫生研究院;

关键词：

fluorous; Mitsunobu; solid phase extraction; triphenylphosphine; diethylazodicarboxylate;

D O I：

10.1016/S0040-4020(02)00205-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H4)(2)PPh] and new [C8F17CH2CH2C6H4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3855 / 3864

页数：10

共 50 条

[1] POLYMER-SUPPORTED ALKYL AZODICARBOXYLATES FOR MITSUNOBU REACTIONS [J].