Compound 5acde

2-(4-(tert-Butyl)phenyl)-3-(4-chlorophenyl)-4-phenyl-5-(4-(trifluoromethyl)phenyl)thiophene

From: Synthesis and characterization of hexaarylbenzenes with five or six different substituents enabled by programmed synthesis

View in PubChem | MDL Molfile | ChemDraw

InChIKey YOXQEGDGHQQBRI-UHFFFAOYSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

A 50-mL Schlenk tube, containing a magnetic stirring bar, was flame-dried under vacuum and filled with nitrogen after cooling to room temperature. To this tube were added Pd(PPh3)4 (10.4 mg, 9.0 μmol, 10 mol%), Ba(OH)2 (30.8 mg, 0.18 mmol, 2.0 equiv), arylboronic acid (0.270 mmol, 3.0 equiv), thiophene-3-yl trifluoromethanesulfonate 4acd (0.09 mmol, 1.0 equiv), dry 1-butanol (3.6 mL) and H2O (3.0 mL) under a stream of nitrogen. The flask was heated at 65 °C for 16 h. After cooling the reaction mixture to room temperature, the mixture was passed through a short silica gel pad (EtOAc). The filtrate was concentrated in vacuo, and the residue was purified by preparative thin-layer chromatography to afford 5acde (34.9 mg, 71% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.45 (d, J = 8.0 Hz, 2H), 7.33–7.23 (m, 4H), 7.21–7.12 (m, 5H), 7.10 (d, J = 8.4 Hz, 2H), 6.95 (dd, J = 7.8, 2.0 Hz, 2H), 6.90 (d, J = 8.4 Hz, 2H), 1.30 (s, 9H); 13C NMR (100 MHz, CDCl3): δ 150.8, 140.4, 140.2, 137.9, 137.7, 136.4, 135.8, 134.7, 132.7, 132.1, 130.6, 130.5, 129.1, 128.9 (q, 2JCF = 32.4 Hz), 128.7, 128.24, 128.18, 127.1, 125.5, 125.3 (q, 3JCF = 3.9 Hz), 124.1 (q, 1JCF = 277 Hz), 34.6, 31.2; HRMS (DART) m/z calcd for C33H27ClF3S [MH]+: 547.14741, found 547.14724.

Back to article page