Azodicarbonyl dimorpholide (ADDM): an effective, versatile, and water-soluble Mitsunobu reagent

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• 作者：Maryanna E. Lanning ; Steven Fletcher
• 关键词：Mitsunobu reaction ; Azodicarbonyl dimorpholide ; ADDM ; Water-soluble ; Green chemistry
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：28 August, 2013
• 年：2013
• 卷：54
• 期：35
• 页码：4624-4628
• 全文大小：4908 K

文摘

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-H₂, may be removed from the reaction mixture by a simple aqueous extraction. Furthermore, we demonstrate that the isolated ADDM-H₂ may be re-oxidized with silver(I) oxide to regenerate ADDM. Finally, a chromatography-free Mitsunobu reaction is presented.