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Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium.
Beilstein J. Org. Chem. 8, 330-336 (2012)
The synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or ether groups are tolerated, and catalytic amounts of hydriodic acid (0.2 equiv) in the presence of 0.6 equiv phosphorous are sufficient to achieve conversion.
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Publication type
Article: Journal article
Document type
Scientific Article
Keywords
Hypohosphorous acid; induced deoxygenation; Organotin compounds; Allylic alcohols; Hydrogen iodide; Reducing system; Derivatives; Phosphorus; Phosphites; Secondary
e-ISSN
1860-5397
Quellenangaben
Volume: 8,
Pages: 330-336
Publisher
Beilstein-Institut zur Förderung der Chemischen Wissenschaften
Reviewing status
Peer reviewed
Institute(s)
PPM-MEX-Molecular EXposomics (MEX)