☆ 4.5 Article

Regioselective hydrocarbonylation of phenylacetylene to α,β-unsaturated esters and thioesters with Fe(CO)5 and Mo(CO)6

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2016)

期刊

JOURNAL OF ORGANOMETALLIC CHEMISTRY

卷 822, 期 -, 页码 67-73

出版社

ELSEVIER SCIENCE SA

DOI: 10.1016/j.jorganchem.2016.01.025

关键词

Hydroalkoxycarbonylation; Hydrothiocarbonylation; Phenylacetylene; Fe(CO)(5); Mo(CO)(6); diazabicyclo[2.2.2]octane (DABCO)

类别

Chemistry, Inorganic & Nuclear Chemistry, Organic

资金

research council of Shiraz University
Iran National Elite Foundation

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摘要

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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