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Second generation fluorous DEAD reagents have expanded scope in the Mitsunobu reaction and retain convenient separation features

Dandapani, S and Curran, DP (2004) Second generation fluorous DEAD reagents have expanded scope in the Mitsunobu reaction and retain convenient separation features. Journal of Organic Chemistry, 69 (25). 8751 - 8757. ISSN 0022-3263

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Abstract

First generation fluorous DEAD reagent bis(perfluorohexylethyl)azo dicarboxylate (C6F13(CH2)2O 2-CN=NCO2(CH2)2C6F13, 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)3O 2CN=NCO2tBu, F-DEAD-2) can be removed by fluorous flash chromatography, and byproducts from bis(perfluorohexylpropyl)azo dicarboxylate (C6F13(CH2)3O 2CN=NCO2(CH2)3C6F 13, 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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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Dandapani, S
Curran, DPcurran@pitt.eduCURRAN
Date: 10 December 2004
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 69
Number: 25
Page Range: 8751 - 8757
DOI or Unique Handle: 10.1021/jo0488098
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Azo Compounds--chemical synthesis; Chromatography, High Pressure Liquid; Fluorine--chemistry; Hydrazines--chemical synthesis; Hydrocarbons, Fluorinated--chemical synthesis; Indicators and Reagents--chemistry; Molecular Structure
PubMed ID: 15575753
Date Deposited: 07 Aug 2013 15:05
Last Modified: 02 Feb 2019 15:59
URI: http://d-scholarship.pitt.edu/id/eprint/19544

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