Regioselectivity Issues in the Addition of Grignard Reagents to Trifluoromethylated α-Bromoenones

Autor:	Dominique Cahard, Alexey R. Romanov, Alexander Yu. Rulev
Rok vydání:	2019
Předmět:	chemistry.chemical_classification Trifluoromethyl Nucleophilic addition 010405 organic chemistry Aryl Organic Chemistry Grignard reaction Regioselectivity 010402 general chemistry 01 natural sciences Medicinal chemistry 3. Good health 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Reagent Physical and Theoretical Chemistry Alkyl
Zdroj:	European Journal of Organic Chemistry. 2019:2143-2149
ISSN:	1434-193X
Popis:	In contrast to non‐fluorinated α‐bromoenones their fluorinated analogs react with alkyl and arylmagnesium bromides leading to saturated CF3‐ketones as major reaction adducts. The regioselectivity of addition depends strongly on the nature of the Grignard reagent. The regioselectivity of addition of organomagnesium reagents to trifluoromethylated α‐bromoenones is reported. Alkyl and aryl Grignard reagents undergo 1,4‐ and/or 1,2‐addition but, in contrast to non‐fluorinated α‐bromoenones, the former direction is dominant for these fluorinated analogs. The high 1,4‐regioselectivity observed in most cases reflects the influence of the trifluoromethyl group on the direction of nucleophilic attack.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::775eda95c2a88e53cc4f3fa5397ab628 https://doi.org/10.1002/ejoc.201900155 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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