643-28-7

Clear pale yellow liquid

ChEBI: 2-Isopropylaniline is an alkylbenzene.

[1] Dr. Huaibo Zhao,  Prof. Daniele Leonori.“Minimization of Back-Electron Transfer Enables the Elusive sp3 C−H Functionalization of Secondary Anilines.” Angewandte Chemie International Edition 60 14 (2021): 7669–7674.

Charge a dry tube equipped with a stirring bar with Ir(dtbbpy)(ppy)2PF6 (4 mg, 4 μmol, 2 mol%), Co(dmgH)(dmgH2)Cl2 (11 mg, 0.03 mmol, 15 mol%), and 2-isopropyl-N-methylaniline (30 mg, 0.20 mmol, 1.0 equiv.); Cap the tube with a Supelco aluminium crimp seal with septum (PTFE/butyl); Evacuate the reaction mixture under high vacuum and backfill with N2 (x 3); Add degassed CH3CN (2.0 mL, 0.1 M), 2-isopropyl-N-methylaniline (30 mg, 0.20 mmol) and Et3N (28 μL, 0.20 mmol, 1.0 equiv.) sequentially to the reaction mixture; Cool the reaction mixture to -78°C and degas by three cycles of freeze, pump (5 min), backfill (with N2), and thaw;
Degas the reaction mixture thoroughly; Seal the vial with parafilm and place approximately 4 cm from blue LEDs; Switch on the blue LEDs and stir the reaction mixture under irradiation without fan for 24 hours; Open the tube and dilute the reaction mixture with H2O (10 mL) and EtOAc (10 mL); Separate the layers and extract the aqueous layer with EtOAc (2 x 10 mL); Wash the combined organic layers with brine (10 mL); Dry the mixture over Na2SO4; Filter the residue and evaporate; Purify the crude product by flash column chromatography on silica gel with hexane-EtOAc to obtain 2-isopropylaniline.^[1]