Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 822, Issue -, Pages 67-73Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2016.01.025
Keywords
Hydroalkoxycarbonylation; Hydrothiocarbonylation; Phenylacetylene; Fe(CO)(5); Mo(CO)(6); diazabicyclo[2.2.2]octane (DABCO)
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Funding
- research council of Shiraz University
- Iran National Elite Foundation
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A highly regioselective hydrocarbonylation of phenylacetylene with thiols and alcohols was developed using metal carbonyls/diazabicyclo[2.2.2]octane ( DABCO) system at 100 degrees C in DMF. The use of Mo(CO)(6) and thiols in the presence of DABCO was applied as an efficient Pd-free method for hydrothiocarbonylation of phenylacetylene into trans-alpha,beta-cinamyl thioesters in excellent yields ( 88-98%). Similar reaction using Fe(CO)(5)/ROH/DABCO system resulted into high yield synthesis of trans-alpha,beta-cinamyl esters ( 87-98%). These reactions were conducted under mild reaction conditions without the need to use gaseous CO or any phosphine ligand and palladium catalyst. (C) 2016 Published by Elsevier B.V.
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