Lewis Acid Promoted Homodimerization of Styrene Diols: An Efficient Approach toward 2-Phenylnaphthalenes

Abstract

We report a straightforward, metal-free, efficient protocol for the synthesis of 2-phenylnaphthalenes from 1-phenylethane-1,2-diols under mild conditions. In this strategy, 1,1,1,3,3,3-hexafluoro-2-propanol is used as a solvent that stabilizes the reaction intermediate. An in situ IR experiment revealed that the reaction proceeds through the formation of phenylacetaldehyde followed by a [4+2] Diels–Alder reaction. Several control experiments were performed to gain mechanistic insights into the reaction.

Key words

phenylnaphthalenes - [4+2]-cycloaddition - Diels–Alder ­reaction - Lewis acid catalysis - phenylethanediols

Publication History

Received: 09 May 2022

Accepted after revision: 26 September 2022

Article published online:
19 October 2022

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• 16 2-Phenylnaphthalene Derivatives 3a–o; General Procedure A dry sealed tube was charged with the appropriate styrene diol derivative 1 (1 equiv, 0.1 mmol). The tube was evacuated with a high-vacuum pump and then filled with N₂ from a balloon. HFIP (0.6 mL), TMSOTf (20 mol%, 3.6 μL), and 1,3-dimethoxybenzene (1.1 equiv, 0.11 mmol) were added sequentially, and the mixture was stirred at 60 °C for 2 h. On completion of the reaction (TLC, 5% EtOAc–hexane), the solvent was removed under reduced pressure to give a crude product that was purified by column chromatography (silica gel, hexane). 2-Phenylnaphthalene (3a) White solid; yield: 18.8 mg (92%); mp 101–102 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.03 (s, 1 H), 7.93–7.81 (m, 3 H), 7.76–7.68 (m, 3 H), 7.47 (td, J = 6.5, 2.9 Hz, 4 H), 7.36 (t, J = 7.4 Hz, 1 H). ¹³C NMR (126 MHz, CDCl₃): δ = 141.1, 138.6, 133.7, 132.6, 128.9, 128.4, 128.2, 127.6, 127.4, 127.3, 126.3, 125.9, 125.8, 125.6.