Rediscovering the Double Friedel–Crafts Acylation: An Expedient Entry to Phenanthrene-9,10-diones

Abstract

The double Friedel–Crafts acylation of readily accessible biaryls with oxalyl chloride delivers the respective phenanthrene-9,10-diones, providing an alternative to the traditional methods, which require harsh oxidizing conditions and multistep sequences. This simple method allows the synthesis of various symmetrical and non-symmetrical targets, and is even effective for the synthesis of the parent ring system from (unactivated) biphenyl.

Key words

cyclization - electrophilic aromatic - substitution - fused-ring systems - Friedel–Crafts acylation - phenanthrene-9,10-diones

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• 15 Typical Procedure: 3,3′-Dimethoxybiphenyl (100 mg, 0.47 mmol) was added to a solution of oxalyl chloride (0.47 mmol) in CH₂Cl₂ (7 mL). Anhyd AlCl₃ (1,4 mmol) was added in one portion and the resulting solution became black. It was stirred at r.t. for 24 h. Then the reaction mixture was poured into a mixture of H₂O (7 mL)/6 N HCl (3 mL), stirred for 15 min and then extracted with CH₂Cl₂ (2 ×). Recombined organic layers were dried (Na₂SO₄) and concentrated. Thereafter the residue was purified by silica gel chromatography (petroleum ether–EtOAc, 3:2) to afford 23b as a yellow-orange powder (37%); mp 132 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.71 (d, J = 8.0 Hz, 1 H), 7.45 (dd, J = 8.0, 8.0 Hz, 1 H), 7.30 (m, 2 H), 7.20 (dd, J = 8.0, 1.3 Hz, 1 H), 7.0 (dd, J = 8.0, 1.3 Hz, 1 H), 3.95 (s, 3 H), 3.85 (s, 3 H). ¹³C NMR (100.6 MHz, CDCl₃): δ = 194.5 (2 × C), 160.0 (2 × C), 158.7 (C), 145.6 (C), 142.0 (C), 131.0 (CH), 129.9 (CH), 129.1 (C), 119.7 (CH), 119.3 (CH), 113.2 (CH), 110.4 (CH), 55.98, 55.43.