Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2’- Diamino-1,1’-binaphthalene in the Presence of Palladium Catalysts

Pálinkás, Noémi and Mikle, Gábor and Aranyi, Anita and Péter, Antal and Kollár, László (2020) Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2’- Diamino-1,1’-binaphthalene in the Presence of Palladium Catalysts. CHEMISTRY SELECT, 5 (35). pp. 11048-11051. ISSN 2365-6549

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Abstract

Palladium-catalysed aminocarbonylation of iodobenzene and 1-iodocyclohexene with both enantiomerically pure and racemic 2,2’-diamino-1,1’-binaphthalene (BINAM) as N-nucleophile was carried out. The mono- and dicarboxamide enantiomers possessing axial chirality were synthesised using (Sax)-BINAM. In the possession of these reference compounds the partial chiral kinetic resolution of racemic BINAM was carried out using various optically active bidentate ligands such as (2S,4S)-BDPP, (2S,3S)-CHIRAPHOS and (R)-BINAP. It was revealed by chiral HPLC measurements that up to 10% enantiomeric excess of carboxamides can be achieved in this way. Although with low enantioselection, enantioselectve aminocarbonylation was carried out for the first time.

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