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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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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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