gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides

Autor: Monika Bilska-Markowska, Marcin Kaźmierczak, Wojciech Jankowski, Marcin Hoffmann
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 2946-2953 (2024)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.20.247
Popis: The incorporation of fluorine atoms within the structure of organic compounds is known to exert a significant impact on their electronic properties, thereby modulating their reactivity in diverse chemical transformations. In the context of our investigation, we observed a striking illustration of this phenomenon. A Michael addition involving gem-difluorovinyl and trifluorovinyl acceptors was successfully achieved, demonstrating high stereoselectivity. This selectivity was further elucidated through theoretical calculations. Using this methodology, a series of new α,β-unsaturated amides, both fluorinated and nonfluorinated, were synthesized.
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