Premium
Highly Chemoselective Calcium‐Catalyzed Propargylic Deoxygenation
Author(s) -
Meyer Vera J.,
Niggemann Meike
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103691
Subject(s) - deoxygenation , chemoselectivity , chemistry , catalysis , triethylsilane , nucleophile , hydride , tertiary alcohols , organic chemistry , hydrogen
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.