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Redox‐Switchable Phase Tags – Facile Mitsunobu Reactions using Ferrocenyl‐Tagged Triphenylphosphine
Author(s) -
Fleckenstein Christoph A.,
Plenio Herbert
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606024
Subject(s) - triphenylphosphine , chemistry , phosphine , redox , ferrocene , mitsunobu reaction , combinatorial chemistry , yield (engineering) , tributylphosphine , organic chemistry , electrochemistry , catalysis , electrode , materials science , metallurgy
Abstract The use of redox‐switched phase tags in ferrocenyl‐substituted triphenylphosphine combined with DBAD (di‐ tert ‐butyl azodicarboxylate) allows high yield (>90 %) Mitsunobu transformations without the need for the chromatographic purification of the products. The redox‐switchable phosphine can be easily synthesized in two steps from 4‐bromoaniline, ferrocene and chlorodiphenylphosphine. It is separated from the reaction mixture by oxidation with iron(III) chloride and can be recycled efficiently by reductive treatment.