Journal Title
Title of Journal: Monatsh Chem
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Abbravation: Monatshefte für Chemie - Chemical Monthly
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Publisher
Springer Vienna
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Authors: Attila Takács Zsuzsanna KabakSolt Gábor Mikle László Kollár
Publish Date: 2014/06/05
Volume: 145, Issue: 9, Pages: 1473-1478
Abstract
Piperidines possessing ester functionality such as 2methoxycarbonylpiperidine methyl pipecolinate 3ethoxycarbonylpiperidine ethyl nipecotate and 4ethoxycarbonylpiperidine ethyl isonipecotate were used as Nnucleophiles in palladiumcatalyzed aminocarbonylation of iodobenzene and iodoalkenes such as 1iodocyclohexene and 17iodoandrost16ene While the aminocarbonylation of both iodoalkenes carried out under mild reaction conditions resulted in the exclusive formation of the carboxamide the same reaction of iodobenzene brought about the mixture of the corresponding carboxamide and 2ketocarboxamide The chemoselectivity toward the latter compounds formed via double carbonyl insertion was substantially increased by using high carbon monoxide pressure up to 40 bar Carboxamides derived from iodoalkenes and ketocarboxamides derived from iodoarene have been obtained in moderate to high yieldsThe authors thank the project ‘Synthesis of supramolecular systems examination of their physicochemical properties and their utilization for separation and sensor chemistry’ SROP422A11/1/KONV20120065 for the financial support This research of A T was supported by the European Union and the State of Hungary cofinanced by the European Social Fund in the framework of TÁMOP 424 A/211120120001 ‘National Excellence Program’
Keywords:
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