d-Glucosamine as a Green Ligand for Palladium-Catalyzed Cross-Coupling of Aryl and Heteroaryl Halides

Abstract

Naturally occurring d-glucosamine works as an efficient green alternative to phosphines in palladium-catalyzed Heck coupling of aryl and heteroaryl halides. An array of trans-stilbene derivatives, aryl naphthyl alkenes, heteroaryl olefins, and β-aryl-substituted acrylates has been synthesized in short reaction times in moderate to high yields.

Key words

green chemistry - cross-coupling - carbohydrates - palladium - transition metals

• References and Notes

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• 25 General Experimental Procedure and Characterization Data for Representative Compounds d-glucosamine (428 mg, 2.0 mmol) was dissolved in DMF–H₂O (1:1, 2 mL). Styrene (0.214 mL, 2.0 mmol), aryl halide (2.0 mmol), K₂CO₃ (3 equiv) and Pd(OAc)₂ (1 mol%) were added to it, and the contents sealed in a vial were irradiated under microwave irradiation at an output power of 100 W for 1 h at 120 °C. The reaction mixture was extracted with hexane (3 × 25mL). The combined organic layers were washed with H₂O, dried over Na₂SO₄, filtered, and concentrated under reduced pressure. Column chromatography on silica gel afforded pure products.(E)-4-(2-Naphthalen-2-ylvinyl)benzonitrile (5b)White crystalline solid. ¹H NMR (300 MHz, CDCl₃): δ = 7.75–780 (m, 4 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.51–7.55 (m, 3 H), 7.41 (t, J = 3.9 Hz, 2 H), 7.28 (d, J = 16.2 Hz, 1 H), 7.08–7.17 (m, 1 H) ppm. ¹³C NMR (75 MHz, CDCl₃): δ = 141.9, 133.8, 133.6, 133.5, 132.54, 132.50, 128.6, 128.2, 127.8, 127.7, 126.99, 126.9, 126.6, 126.5, 123.3, 119.1, 110.6 ppm. MS (EI): m/z = 256 [M + 1].(E)-2-(2-o-Tolylvinyl)naphthalene (5c)White crystalline solid. ¹H NMR (300 MHz, CDCl₃): δ = 7.731 (s, 2 H), 7.68–7.71 (m, 2 H), 7.64 (d, J = 8.7 Hz, 1 H), 7.54 (d, J = 6.9 Hz, 1 H), 7.34–7.38 (m, 2 H), 7.31–7.33 (m, 1 H), 7.12–7.16 (m, 1 H), 7.02–7.11 (m, 3 H), 2.36 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 136.5, 135.9, 135.2, 133.8, 133.1, 130.6, 130.1, 128.4, 128.1, 127.8, 127.7, 126.9, 126.7, 126.4, 126.3, 125.9, 125.4, 123.7, 20.1. MS (EI): m/z = 244.