Palladium-catalyzed allylation of trifluoromethylated ketene aminoacetals

Visible Light-Induced Photoredox Construction of Trifluoromethylated Quaternary Carbon Centers from Trifluoromethylated Tertiary Bromides

“…With the aim of providing versatile methodologies for constructing TFQC, ,,,, we recently reported a Pd-catalyzed allylation reaction of trifluoromethyl-containing nucleophilic building blocks (Scheme ). This reaction took place via strong electrophilic π-allyl palladium species. We envisioned that the trifluoromethyl-containing nucleophilic building blocks we used could be brominated, leading to umpolung reactive center.…”

“…We generated the trifluoromethylated tertiary bromides ( 3 ) by direct bromination with NBS of the trifluoromethyl-containing nucleophilic building-block ( 1 ) derived from industrial waste perfluoroisobutylene (Table ). Reactions took place smoothly in DMF, and reactant 1 was fully converted within 3 h, giving the trifluoromethylated tertiary bromides in good to excellent yields. The alkyl ( 3c , 3d , 3e , 3g )- and aryl ( 3f )-substituted groups on the oxazolyl ring were all tolerated.…”

“…With the aim of providing versatile methodologies for constructing TFQC, ,,,, we recently reported a Pd-catalyzed allylation reaction of trifluoromethyl-containing nucleophilic building blocks (Scheme ). This reaction took place via strong electrophilic π-allyl palladium species.…”

Visible Light-Induced Radical Cyclization of Tertiary Bromides with Isonitriles To Construct Trifluoromethylated Quaternary Carbon Center

“…We have shown great interest in using α-trifluoromethylated carbanions, which are challenging starting materials, with a facile defluorination before further functionalization. Iridium catalyst, palladium catalyst, and organocatalyst have proven to be a successful approach to TFQC. However, normally highly electrophilic substrates such as electron deficient olefins are needed, which has limited the application.…”

2,2,2-Trifluoroethylation of Styrenes with Concomitant Introduction of a Hydroxyl Group from Molecular Oxygen by Photoredox Catalysis Activated by Visible Light

“…Within our investigations on the organic transformation at the neighboring carbon to a CF 3 group, we were interested in activating 1,1,1-trifluoro-2-iodoethane (CF 3 CH 2 I, 1 ) to a radical using visible-light-induced photoredox catalysis. We have already reported the sulfinatodehalogenation of 1 with alkyl-substituted alkenes and that this reaction cannot be applied to styrenes .…”