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Iron Pentacarbonyl in Alkoxy- and Aminocarbonylation of Aromatic Halides

Matej Babjak*, Oľga Caletková, Diana Ďurišová, Tibor Gracza

*Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia, Email: matej.babjakstuba.sk

M. Babjak, O. Caletková, D. Ďurišová, T. Gracza, Synlett, 2014, 25, 2579-2584.

DOI: 10.1055/s-0034-1379227 (free Supporting Information)



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Abstract

Optimized reaction conditions for a Heck-type carbonylation of (hetero)aryl bromides with [Fe(CO)5] enable alkoxycarbonylations in the presence of methanol and butanol and aminocarbonylations in the presence of various amines, including aniline and benzotriazole, with reasonable results.

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Note

As far as we have tested, in the case of a chloride on an activated position in a heterocycle (e.g. 2- position in pyridine or 4-posidion in pyrimidine), the method works with results similar to bromides.

Matej Babjak, January 18, 2016


Key Words

aminocarbonylation, methoxycarbonylation, carbonylation, carbonyl complexes, iron, palladium catalysis, multicomponent reactions


ID: J60-Y2014