An unusual reaction of α-alkoxyphosphonium salts with Grignard reagents under an O2 atmosphere

Hiromichi Fujioka; Akihiro Goto; Kazuki Otake; Ozora Kubo; Yoshinari Sawama; Tomohiro Maegawa

doi:10.1039/C1CC13919C

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An unusual reaction of α-alkoxyphosphonium salts with Grignard reagents under an O₂ atmosphere†

Hiromichi Fujioka,*^a Akihiro Goto,^a Kazuki Otake,^a Ozora Kubo,^a Yoshinari Sawama ‡^a and Tomohiro Maegawa^a

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan
E-mail: fujioka@phs.osaka-u.ac.jp
Fax: +8168798229
Tel: +8168798225

Abstract

An unusual and novel reaction of α-alkoxyphosphonium salts, generated from O,O-acetals and Ph₃P, with Grignard reagents under an O₂ atmosphere afforded alcohols in moderate to high yields. It was clarified by isotopic labelling experiments that the reaction proceeded via a novel radical pathway.

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Article information

DOI: https://doi.org/10.1039/C1CC13919C
Article type: Communication
Submitted: 01 Jul 2011
Accepted: 19 Jul 2011
First published: 04 Aug 2011

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Chem. Commun., 2011,47, 9894-9896

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An unusual reaction of α-alkoxyphosphonium salts with Grignard reagents under an O₂ atmosphere

H. Fujioka, A. Goto, K. Otake, O. Kubo, Y. Sawama and T. Maegawa, Chem. Commun., 2011, 47, 9894 DOI: 10.1039/C1CC13919C

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