Journal
TETRAHEDRON LETTERS
Volume 54, Issue 35, Pages 4624-4628Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.06.049
Keywords
Mitsunobu reaction; Azodicarbonyl dimorpholide; ADDM; Water-soluble; Green chemistry
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Funding
- University of Maryland School of Pharmacy
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One of the caveats of the Mitsunobu reaction is the often difficult and laborious purification of the reaction mixture. Herein, we show that azodicarbonyl dimorpholide (ADDM) is an effective and versatile Mitsunobu reagent, which, along with its reduced form ADDM-H-2, may be removed from the reaction mixture by a simple aqueous extraction. Furthermore, we demonstrate that the isolated ADDM-H-2 may be re-oxidized with silver(I) oxide to regenerate ADDM. Finally, a chromatography-free Mitsunobu reaction is presented. (C) 2013 Elsevier Ltd. All rights reserved.
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