Intramolecular Cycloisomerization of Aryl-Substituted Alkylidenecyclo­propanes via NHC Palladium-Catalyzed Cascade C-C Bond Cleavage/C-H Activation/C-C Bond Formation

Abstract

A well-defined N-heterocyclic carbene (NHC) palladium-catalyzed intramolecular cyclization reaction of aryl-substituted alkylidenecyclopropanes (ACP) to 1-aryl dihydronaphthalenes is described. The NHC salts were found to suppress β-hydride elimination from the homoallylpalladium intermediate, which may lead to unwanted alkene formation. A plausible mechanism for the cycloisomerization was proposed.

Key words

ring opening - cycloisomerization - N-heterocyclic carbene - alkylidenecyclopropanes - dihydronaphthalenes

References and Notelos

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17

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): ν_max = 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) ų, crystal size: 0.482 × 0.435 × 0.276 mm, T = 293 (2) K, Z = 4, reflections collected/unique: 10650/ 3977 (R _int = 0.0921), data: 3977, restraints: 0, parameters: 222.