Compound 9A

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InChIKey KQQNFNIVQFKQMG-UHFFFAOYSA-N

Compound data: CIF

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

A 7-mL screw cap 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 tetraarylthiophene S-oxide 6acde (1.0 equiv), diarylethyne 7A (2.0 equiv) and mesitylene under a stream of nitrogen. The flask was heated at 160 °C for 48 h. After cooling the reaction mixture to room temperature, the mixture was concentrated in vacuo and the residue was purified by preparative thin-layer chromatography (hexane/EtOAc = 1:1) to afford 9A (5.6 mg, 27% yield) as a white solid from 6acde (17.0 mg, 0.030 mmol), 7A (10.8 mg, 0.060 mmol) and mesitylene (200 μL). ¹H NMR (600 MHz, CDCl₃): δ 8.19–8.10 (m, 4H), 7.16 (d, J = 8.4 Hz, 2H), 6.95–6.89 (m, 7H), 6.85 (d, J = 8.4 Hz, 2H), 6.77–6.70 (m, 8H), 6.67 (d, J = 8.4 Hz, 2H), 1.34 (s, 9H); ¹³C NMR (150 MHz, CDCl₃): δ 149.4, 148.8, 148.5, 148.0, 147.8, 143.1, 141.4, 141.0, 140.7, 138.9, 138.7, 138.0, 137.5, 137.0, 135.5, 132.3, 131.7, 131.3, 130.9, 130.5, 128.2 (q, ²J_CF = 31.7 Hz), 127.2, 127.0, 126.2, 126.0, 125.9, 124.1, 124.0 (q, ³J_CF = 2.9 Hz), 123.9 (q, ¹J_CF = 274 Hz), 34.3, 31.1; HRMS (APCI) m/z calcd for C₄₅H₃₄ClF₃N₂[MH]⁺: 695.2435, found 695.2435.