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Synlett 2023; 34(06): 629-634
DOI: 10.1055/s-0042-1751376
DOI: 10.1055/s-0042-1751376
cluster
Chemical Synthesis and Catalysis in India
Lewis Acid Promoted Homodimerization of Styrene Diols: An Efficient Approach toward 2-Phenylnaphthalenes
The authors thank the Science and Engineering Research Board (SERB), New Delhi, India, for financial support in the form of a Start-up Research Grant (File No.: SRG/2019/000213). They also thank IIT Delhi, New Delhi, for the institute’s seed grant money. R.M., J.K., and A.T. are grateful to CSIR/UGC (MHRD), India, for their research fellowships.
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 - phenylethanediolsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751376.
- Supporting Information
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.