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Regioselectivity Issues in the Addition of Grignard Reagents to Trifluoromethylated α‐Bromoenones
Author(s) -
Romanov Alexey R.,
Cahard Dominique,
Rulev Alexander Yu.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900155
Subject(s) - regioselectivity , chemistry , reagent , nucleophile , trifluoromethyl , aryl , nucleophilic addition , trifluoromethylation , grignard reagent , alkyl , organic chemistry , combinatorial chemistry , catalysis
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.