Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 15, Pages 4687-4691Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103691
Keywords
alcohols; calcium; chemoselectivity; direct deoxygenation; reduction
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A calcium-catalyzed direct reduction of propargylic alcohols and ethers has been accomplished by using triethylsilane as a nucleophilic hydride source. At room temperature a variety of secondary propargylic alcohols was deoxygenated to the corresponding hydrocarbons in excellent yields. Furthermore, for the first time, a catalytic deoxygenation of tertiary propargylic alcohols was generally applicable. The same protocol was suitable for an efficient reduction of secondary as well as tertiary propargylic methyl, benzyl and allyl ethers. Substrates containing an additional keto-, ester or secondary hydroxyl function were reduced with exceptional chemoselectivity at the propargylic position.
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