Phosphine-Triggered Selectivity Switch in Silver-Catalyzed o-Alkynylbenzohydroxamic Acid Cycloisomerizations.
Fiche publication
Date publication
octobre 2016
Journal
Organic letters
Auteurs
Membres identifiés du Cancéropôle Est :
Dr BOURDERIOUX Aurélie
Tous les auteurs :
Bantreil X, Bourderioux A, Mateo P, Hagerman CE, Selkti M, Brachet E, Belmont P
Lien Pubmed
Résumé
A silver-catalyzed cycloisomerization reaction of a series of o-alkynylbenzohydroxamic acids is reported. Several 5-exo-dig and 6-endo-dig modes of cyclization were observed with the nitrogen or oxygen atoms of the amide group acting as nucleophiles. The selectivity was strongly dependent on the silver salt used and on the presence of triphenylphosphine as an additive. Indeed, while the use of AgO at room temperature allowed the isolation of isobenzofuran-1-one oximes (7 compounds, 48-92% yield), [Ag(Im)] with the concomitant addition of 2 equiv of PPh led to a switch in selectivity and to a family of isoindolin-1-ones (10 compounds, 59-87%).
Référence
Org Lett. 2016 10 7;18(19):4814-4817