Compound 3aa

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: Crystallographic data

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

The photocatalyst Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆ (1 mol%), the gold(i) complex (p-CF₃Ph)₃PAuCl (5 mol%), K₂CO₃ (2.5 equiv), 1,10-Phenanthroline (10 mol%), the appropriate iodoalkynes 2 (0.15 mmol) and o-alkynylphenol derivative 1 (0.1 mmol) were introduced in a Schlenk tube equipped with a magnetic stirring bar in which MeCN (2 ml) was added. The mixture was degassed using three freeze pump–thaw cycles and purged with Ar, then irradiated with blue LEDs light (a very simple irradiating setup used as depicted in pictures below) for 16 h (unless mentioned). The stirring speed is equal or more than 1,200 r.p.m. The reaction was quenched with Et₂O (3 ml) and a 2 M HCl solution (3 ml) and the solution was extracted by Et₂O (3 × 5 ml). The combined organic layer was dried over MgSO₄, filtered and concentrated under reduced pressure to give the crude product. The residue was purified by FC on silica gel to afford the desired product or determined by ¹H NMR using 1,3,5-trimethoxybenzene as internal standard. Following general procedure GP4 outlined above with 2-(p-tolylethynyl)phenol 1a (20.8 mg, 0.1 mmol) and (iodoethynyl)benzene 2a (34.2 mg, 0.15 mmol) the crude product was purified by flash column chromatography (100% Pent) to afford 3aa as a white solid (22 mg, 71%). Mp 117 ^oC. ¹H NMR (400 MHz, CDCl₃) δ 8.25 (d, J = 8.4 Hz 2H), 7.76-7,74 (m, 1H), 7.65-7.62 (m, 2H), 7.53-7.51 (m, 1H), 7.44-7.38 (3H), 7.37-7.30 (m, 4H), 2.44 (s, 3H); ¹³C NMR (101 MHz, CDCl₃) δ 156.7, 153.4, 139.4, 131.5, 130.0, 129.4, 128.5, 128.3, 127.5, 126.0, 125.1, 123.5, 123.3, 120.2, 111.1, 98.4, 96.5, 81.4, 21.5; IR (ATR) 2920, 2852, 2210, 1739, 1453, 1378, 1243, 1192, 1097, 820, 810, 739, 880 cm^-1; HRMS (APCI) calc. for C₂₃H₁₇O⁺ [M+H]⁺: 309.1274, found 309.1278.