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Palladium-Catalyzed Selective Carbonylation Reactions of Ortho-Phenylene Dihalides with Bifunctional N,O-Nucleophiles

Year: 2024

Type: article

Abstract: Palladium-catalyzed carbonylation reactions of ortho-phenylene dihalides were studied using aminoethanols as heterobifunctional N,O-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be selectively realized under optimized conditions, enabling the formation of amide alcohols, and the challenging alkoxycarbonylation can also be proved feasible, enabling amide-ester production. Intramolecular double carbonylation reaction can be achieved using 1,2-diiodobenzene and amino alcohols featuring secondary amine groups, giving oxazocine derivatives. Useful reaction scope with various amino alcohols was performed with good isolated yields of the targeted compounds. Intramolecular C-O coupling of amide alcohols possessing bromo substituent in adjacent ortho position is also demonstrated as a potential next step in benzoxazepine heterocycle formation.

Source: Molecules

DOI: 10.3390/molecules29235620

Authors: Fanni Bede, Attila Takács, László Kollár, Péter Pongrácz

Institution: University of Pecs

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,069

Funders: Pécsi Tudományegyetem, Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, Innovációs és Technológiai Minisztérium, Nemzeti Kutatási, Fejlesztési és Innovaciós Alap