Cryptand-22 as an Efficient Ligand for the Palladium-Catalyzed Mizoroki–Heck Reaction under Air

Abstract

An efficient catalytic system for the Mizoroki–Heck cross-coupling reaction was developed based on the air- and heat-stable palladium(II) chloride–cryptand 22 complex. The complex is a highly active catalyst for coupling of aryl iodides, bromides, or chlorides with various olefins.

Key words

Heck reaction - cross-coupling - halides - olefins - cryptands - catalysis

• References and Notes

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• 15 Aralkenes 3; General Procedure A 5 mL round-bottomed flask was charged with aryl halide 1 (1 mmol), alkene 2 (1.1 mmol), PdCl₂–cryptand 22 (0.009 mmol, 0.9 mol%), Et₃N (1.1 mmol), and DMF (1 mL). [For aryl bromides or chlorides, TBAB (1 mmol) was also added]. The mixture was stirred at 130 °C for the appropriate time (Table 2) while the progress of the reaction was monitored (TLC). Upon completion of the reaction, the mixture was cooled to r.t., poured into H₂O (10 mL), and extracted with CH₂Cl₂ (3 × 8 mL). The combined organic extracts were washed with brine (2 × 8 mL), dried (MgSO₄), and concentrated. Purification by preparative TLC [silica gel, hexane or hexane–EtOAc (9:1)] gave the pure product. 1-Methyl-4-[(E)-2-phenylvinyl]benzene (3e) White solid; yield: 175 mg (90%); mp 119–122 °C (Lit.^2a 120–122 °C). ¹H NMR (300 MHz, CDCl₃): δ = 2.41 (s, 3 H), 7.13 (s, 2 H), 7.22 (d, J = 7.9 Hz, 2 H), 7.29 (t, J = 7.3 Hz, 1 H), 7.40 (t, J = 7.3 Hz, 2 H), 7.47 (d, J = 7.9 Hz, 2 H), 7.55 (d, J = 7.4 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 21.3, 126.45, 126.49, 127.5, 127.7, 128.65, 128.7, 129.5, 134.6, 137.55, 137.57. 1-Methyl-2-[(E)-2-phenylvinyl]benzene (3f) Pale-yellow oil; yield: 138 mg (72%). ¹H NMR (300 MHz, CDCl₃): δ = 2.51 (s, 3 H), 7.08 (d, J = 16.1 Hz, 1 H), 7.26–7.47 (m, 7 H), 7.61 (d, J = 7.6 Hz, 2 H), 7.68 (d, J = 6.5 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 20.0, 125.4, 126.3, 126.6, 126.7, 127.65, 127.69, 128.8, 130.1, 130.5, 135.9, 136.5, 137.8. 1-Methoxy-4-[(E)-2-phenylvinyl]benzene (3g) White solid; yield: 168 mg (80%); mp 136–137 °C (Lit.¹⁸ 135–137 °C). ¹H NMR (300 MHz, CDCl₃): δ = 3.85 (s, 3 H), 6.89–6.94 (m, 2 H), 6.99 (d, J = 16.3 Hz, 1 H), 7.09 (d, J = 16.3 Hz, 1 H), 7.23–7.28 (m, 1 H), 7.36 (t, J = 7.7 Hz, 2 H), 7.45–7.52 (m, 4 H). ¹³C NMR (75 MHz, CDCl₃): δ = 55.3, 114.1, 126.3, 126.6, 127.2, 127.7, 128.2, 128.7, 130.1, 137.7, 159.3. Butyl (2E)-3-(4-Methoxyphenyl)acrylate (3i) Colorless oil; yield: 200 mg (92%). ¹H NMR (300 MHz, CDCl₃): δ = 0.97 (t, J = 7.3 Hz, 3 H), 1.43 (sext, J = 7.4 Hz, 2 H), 1.70 (quin, J = 6.6 Hz, 2 H), 2.34 (s, 3 H), 4.20 (t, J = 6.6 Hz, 2 H), 6.39 (d, J = 16.0 Hz, 1 H), 7.16 (d, J = 8.0 Hz, 2 H), 7.40 (d, J = 8.0 Hz, 2 H), 7.66 (d, J = 16.0 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 13.8, 19.2, 21.4, 30.8, 64.3, 117.2, 128.0, 129.6, 131.7, 140.5, 144.5, 167.2. Butyl (2E)-3-(2-Thienyl)acrylate (3j) Pale-yellow oil; yield: 197 mg (94%). ¹H NMR (300 MHz, CDCl₃): δ = 0.96 (t, J = 7.3 Hz, 3 H), 1.43 (sext, J = 7.2 Hz, 2 H), 1.68 (quin, J = 6.8 Hz, 2 H), 4.19 (t, J = 6.6 Hz, 2 H), 6.24 (d, J = 15.7 Hz, 1 H), 7.04 (t, J = 4.9 Hz, 1 H), 7.24–7.27 (m, 1 H), 7.36 (d, J = 4.9 Hz, 1 H), 7.77 (d, J = 15.7 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 13.8, 19.2, 30.8, 64.4, 117.0, 128.1, 128.3, 130.8, 137.0, 139.6, 166.9. 4-[(E)-2-Phenylvinyl]benzonitrile (3q) White solid; yield: 168 mg (82%); mp 115–118 °C (Lit.²¹ 116–118 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.09 (d, J = 16.3 Hz, 1 H), 7.23 (d, J = 16.3 Hz, 1 H), 7.26–7.42 (m, 3 H), 7.53–7.66 (m, 6 H). ¹³C NMR (75 MHz, CDCl₃): δ = 110.6, 119.1, 126.7, 126.88, 126.94, 128.7, 128.9, 132.4, 132.5, 136.3, 141.8. 4-[(E)-2-Phenylvinyl]benzaldehyde (3r) Pale-yellow solid; yield: 176 mg (85%); mp 117–118 °C (Lit.²² 115–116 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.15 (d, J = 16.3 Hz, 1 H), 7.28 (d, J = 16.3 Hz, 1 H), 7.32–7.42 (m, 3 H), 7.56 (d, J = 7.2 Hz, 2 H), 7.66 (d, J = 7.7 Hz, 2 H), 7.88 (d, J = 7.7 Hz, 2 H), 10.0 (s, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 126.9, 127.3, 128.5, 128.9, 130.3, 132.2, 135.3, 136.5, 143.4, 191.7. 1-{4-[(E)-2-Phenylvinyl]phenyl}ethanone (3t) Pale-yellow solid; yield: 142 mg (64%); mp 143–145 °C (Lit.²² 144–145 °C). ¹H NMR (300 MHz, CDCl₃): δ = 2.62 (s, 3 H), 7.13 (d, J = 16.3 Hz, 1 H), 7.24 (d, J = 16.3 Hz, 1 H), 7.28–7.33 (m, 1 H), 7.39 (t, J = 7.2 Hz, 2 H), 7.54 (d, J = 7.8 Hz, 2 H), 7.59 (d, J = 8.2 Hz, 2 H), 7.96 (d, J = 8.2 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 26.6, 126.5, 126.8, 127.4, 128.3, 128.8, 128.9, 131.5, 135.9, 136.7, 142.0, 197.5.
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