Compound 8d
(4-hydroxy-3-methyl-2-(phenylethynyl)phenyl)(pyrrolidin-1-yl)methanone
From: Catalytic activation of unstrained C(aryl)–C(aryl) bonds in 2,2′-biphenols
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Compound data: 1H NMR
Compound data: 13C NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Method B: To a 4.0 mL vial charged with a stir bar, 1.0 equiv. of halogenated phenol (3ah or 3ai), 2.0 equiv. of the corresponding organotin reagent, 10 mol% of Pd(PtBu3)2 and 1,4-dioxane (0.5 mL/25 mg) were added in glovebox. The vail was then heated to 100 oC and monitored by TLC. After the reaction was completed, the mixture was concentrated and purified by silica gel chromatography (hexane/acetone = 2/1) to give the corresponding products. 3ai (20 mg, 0.060 mmol) and tributyl(phenylethynyl)tin (47.3 mg, 0.12 mmol) were subjected to Method B outlined above to give the corresponding phenol 8d as a white solid (14.9 mg, 81% yield). m.p. 193-194 oC. 1H NMR (500 MHz, CDCl3) δ 8.93 (s, 1H), 7.45 – 7.43 (m, 2H), 7.38 – 7.28 (m, 3H), 6.81 (d, J = 8.0 Hz, 1H), 6.59 (d, J = 8.5 Hz, 1H), 3.70 (t, J = 7.0 Hz, 2H), 3.35 – 3.32 (m, 2H), 2.36 (s, 3H), 1.96 – 1.89 (m, 2H), 1.86 – 1.80 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 170.3, 155.7, 131.7, 131.4, 128.4, 128.3, 127.8, 124.0, 123.3, 120.5, 116.4, 95.6, 86.2, 48.3, 45.9, 25.9, 24.7, 14.0. HRMS-APCI: [M+H]+ Calculated for C20H20NO2+ 306.1489, Found: 306.1492. IR (film, cm-1) 3157, 2974, 2879, 2243, 1602, 1570, 1492, 1443, 1340, 1309, 1264, 1175, 1061.
