The Goldilocks Principle in Phase Labeling. Minimalist and Orthogonal Phase Tagging for Chromatography-Free Mitsunobu Reaction

Mariann Szigeti, Zoltán Dobi, T. Soós

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

An inexpensive and chromatography-free Mitsunobu methodology has been developed using low molecular weight and orthogonally phase-tagged reagents, a tert-butyl-tagged highly apolar phosphine, and a water-soluble DIAD analogue. The byproduct of the Mitsunobu reactions can be removed by sequential liquid-liquid extractions using traditional solvents such as hexanes, MeOH, water, and EtOAc. Owing to the orthogonal phase labeling, the spent reagents can be regenerated. This new variant of the Mitsunobu reaction promises to provide an alternative and complementary solution for the well-known separation problem of the Mitsunobu reaction without having to resort to expensive, large molecular weight reagents and chromatography.

Original languageEnglish
Pages (from-to)2869-2874
Number of pages6
JournalJournal of Organic Chemistry
Volume83
Issue number5
DOIs
Publication statusPublished - Mar 2 2018

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Chromatography
Labeling
phosphine
Molecular weight
Water
Liquids
Hexanes
Byproducts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

The Goldilocks Principle in Phase Labeling. Minimalist and Orthogonal Phase Tagging for Chromatography-Free Mitsunobu Reaction. / Szigeti, Mariann; Dobi, Zoltán; Soós, T.

In: Journal of Organic Chemistry, Vol. 83, No. 5, 02.03.2018, p. 2869-2874.

Research output: Contribution to journalArticle

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