3-Trifluoromethylindoline-2-one derivatives were prepared in a visible-light photocatalytic transformation of acrylamides. The arylation-cyclization sequence was initiated
The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.
The term and concept of Ortho Effect (OE) is introduced for the description of steric effects in transition metal catalyzed directed ortho C–H activation reactions to explain and predict reactivities of substrates.
Development of direct late-stage installation of key fluorinated functional groups into aromatic systems is an important and challenging task of current organic chemistry. Herein, we report a novel palladium catalyzed trifluoroethylation process by C-H activation for the access of ortho trifluoroethylated aromatic ureas. The application of novel, highly active trifluoroethyl(mesityl)iodonium salt enables the efficient introduction of the trifluoroethyl group at 25 °C in 3 hours in high yields (up to 95%) with good functional group tolerance. Abstract: Development of direct late-stage installation of key fluorinated functional groups into aromatic systems is an important and challenging task of current organic chemistry. Herein, we report a novel palladium catalyzed
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