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Synfacts 2008(8): 0892-0892  
DOI: 10.1055/s-2008-1077928
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Purification-Free Synthesis of Aryl Ethers via the Mitsunobu Reaction

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
E. Valeur*, D. Roche
Merck-Serono, chilly-Mazarin, France
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

The Mitsunobu reaction of phenols 1 with diols 2 was examined with commercially available polymer-supported triphenylphosphine (Polymer Laboratories, 1.50 mmol/g, 3.0 equiv) and N,N,N′,N′-tetramethylazodicarbonamide (TMAD, 1.5 equiv) to give the corresponding aryl ethers 3 in up to 97% yield with 100% purity (9 examples). The use of polymer-supported tri­phenylphosphine from different suppliers (Novabiochem and Fluka) gave poor results.