1,4-Diphenylbutane Used in the Synthesis of 1-Arylnaphthalenes and 4-Arylcoumarins
Diao H, et al. Helvetica Chimica Acta, 2021, 104(7), e2100056.
Using 1,4-diphenylbutane as a linear substrate, 1-arylnaphthalenes and 4-arylcoumarins can be successfully constructed, by iron-catalyzed intramolecular cross-dehydroarylation (CDA) between benzyl C(sp3)H bonds and aromatic C(sp2)H bonds. In addition, introducing different functional groups into 1,4-diphenylbutane as the substrate can be further used to form a variety of expected products, such as polycyclic aromatic hydrocarbons with significant optoelectronic properties.
General Synthesis Procedures
· To a 25 mL oven-dried Schlenk tube with magnetic stir bar, FeCl3 (2.5 mol%), DDQ (5.0 equiv) was added, then the 1,4-diphenylbutane substrate (0.2 mmol, 1.0 equiv) and 2.0 mL DCE were added to the reaction mixture successively.
· Subsequently the tube was pumped 3 times on the vacuum line with nitrogen. The tube was sealed and stirred at 100 °C for 36 hours. The reaction mixture was cooled to room temperature, diluted with 10 mL DCM, filtered, and rinse with an appropriate amount of DCM. The filtrate was concentrated and purified by flash column chromatography on silica gel.