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Synlett 2010(5): 801-803  
DOI: 10.1055/s-0029-1219194
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical One-Pot Transformation of Triphenylphosphine Oxide to Triphenylphosphine by Reduction of in situ Generated Triphenylphosphine Dichloride

Tomotake Yano, Masakatsu Hoshino, Manabu Kuroboshi, Hideo Tanaka*
Department of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima-naka 3-1-1, Okayama 700-8530, Japan
Fax: +81(86)2518079; e-Mail: tanaka95@cc.okayama-u.ac.jp;
Further Information

Publication History

Received 9 November 2009
Publication Date:
14 January 2010 (online)

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Abstract

One-pot transformation of triphenylphosphine oxide to triphenylphosphine was achieved by the reaction of triphenylphosphine oxide with oxalyl chloride, which led to the formation of triphenylphosphine dichloride, and subsequent reduction of triphenylphosphine dichloride with a combination of aluminum-catalytic metal salt.

Key words

triphenylphosphine - triphenylphosphine oxide - reduction - aluminum - multi redox system

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Recently, the authors reported electrochemical reduction of triphenylphosphine dichloride to triphenylphosphine. Yano, T.; Kuroboshi, M.; Tanaka, H. Tetrahedron Lett. in press.

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Triphenylphosphine oxide 2 was obtained by the hydrolysis of triphenylphosphine dichloride 3 in the workup procedure.