Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Conversion of Alcohols to Alkyl Aryl Sulfides by a New Type of Oxidation–Reduction Condensation Using Phenyl Diphenylphosphinite
Kiichi KurodaYuji MaruyamaYujiro HayashiTeruaki Mukaiyama
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2009 Volume 82 Issue 3 Pages 381-392

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Abstract

Preparation of alkyl aryl sulfides from alcohols and arenethiols such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation–reduction condensation using phenyl diphenylphosphinite (PhOPPh2) and benzoquinone derivatives or azide compounds. This reaction proceeds under mild and neutral conditions and is applicable to the thioetherification of various alcohols in which the chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configuration.

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© 2009 The Chemical Society of Japan
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