Efficient, mild, parallel and purification-free synthesis of aryl ethers via the Mitsunobu reaction

A wide range of commercial diazodicarboxylates and phosphines were screened in an attempt to find purification-free conditions for application in parallel synthesis. The combination of immobilized triphenylphosphine and TMAD proved to be suitable for the synthesis of aryl ethers via the Mitsunobu re...

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Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 26; pp. 4182 - 4185
Main Authors Valeur, Eric, Roche, Didier
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.06.2008
Elsevier
Subjects
Aryl ethers
Chemistry
Chemistry, Organic
Mitsunobu
Parallel synthesis
Physical Sciences
Polymer-supported
Purification-free
Science & Technology
TMAD
TAP
PS
Parallel synthesis
Polymer-supported
DAP-DP
TBS
DIAD
Mitsunobu
ADDP
Aryl ethers
DEAD
TMAD
Purification-free
DBAD
AZODICARBOXYLATE
REAGENTS
MECHANISM
SOLID-PHASE SYNTHESIS
purification-free
LEAD OPTIMIZATION
polymer-supported
ESTERIFICATION REACTION
TRIPHENYLPHOSPHINE
CHROMATOGRAPHY
aryl ethers
parallel synthesis
ALCOHOLS
COMBINATORIAL CHEMISTRY
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Summary:A wide range of commercial diazodicarboxylates and phosphines were screened in an attempt to find purification-free conditions for application in parallel synthesis. The combination of immobilized triphenylphosphine and TMAD proved to be suitable for the synthesis of aryl ethers via the Mitsunobu reaction. Nine ethers were synthesized in good yield and excellent purity, the purification being limited to a filtration step.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.04.099