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Preparation of 4-Phenyl-1,2-dihydronaphthalene
(2a) and (1-Phenylbuta-1,3-dienyl)benzene
(3a); Typical Procedure
Under an N2 atmosphere, a mixture of 1a (206 mg, 1 mmol), Cl2PdL2 (20 mg, 0.02 mmol), IMes·HCl (35 mg, 0.08 mmol) and DMA (2 mL) was stirred for 12 h at 160 °C. The reaction was monitored by TLC (eluent: hexane). After the reaction was judged complete, the reaction mixture was allowed to cool. The crude mixture was then loaded directly onto SiO2 and purified by column chromatography using hexane as the eluent to give the products 2a (86 mg, 42%) and 3a (14 mg, 7%).
Compound 2a: colorless oil. IR (film): νmax = 3059, 3026, 2934, 1720, 1662, 1597, 1489, 1447, 1269, 1157 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.49-7.09 (m, 5 H), 7.00 (d, J = 7.4 Hz, 1 H), 6.08 (t, J = 4.7 Hz, 1 H), 2.84 (t, J = 8.1 Hz, 2 H), 2.42-2.37 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 140.8, 139.7, 136.8, 135.1, 128.7, 128.2, 127.6, 127.5, 127.0, 126.9, 126.2, 125.4, 28.3, 23.5.MS (EI): m/z (%) = 207 (22.1) [M+ + 1], 206 (100) [M+], 191 (51.3), 128 (26.7), 91 (47.6). ESI-HRMS: m/z calcd for C16H14 [M+]: 206.1096; found: 206.1099.
Compound 3a: colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.38-7.20 (m, 10 H), 6.71 (d, J = 11.0 Hz, 1 H), 6.43 (m, 1 H), 5.38 (ddd, J = 16.8, 0.7, 0.7 Hz, 1 H), 5.11 (ddd, J = 10.2, 0.9, 0.76 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 143.1, 142.1, 139.6, 134.9, 130.4, 128.5, 128.2, 128.1, 127.6, 127.5, 127.4, 118.6.
18 The crystal data of 2f have been deposited at the CCDC with number 671565. Crystal data for 2f: C22H26O2, MW = 322.43, monoclinic, space group P2(1)/c, final R indices [I > 2σ(I)], R1 = 0.0505, wR2 = 0. 1033, a = 14.8134(19) Å, b = 16.2215(19) Å, c = 7.7787(10) Å, α = 90°, β = 100.708(2)°, γ = 90°, V = 1836.6(4) Å3, crystal size: 0.482 × 0.435 × 0.276 mm, T = 293 (2) K, Z = 4, reflections collected/unique: 10650/ 3977 (R
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