Regioselective Synthesis of α-Phosphinoylnaphthols through Rhodium-Catalyzed Annulation of 1-Alkynylphosphine Oxides with Sulfoxonium Ylides

Wucheng Xie; Binting Lin; Xinyi Jian; Qinhong Lin; Junjun Shi

doi:10.1055/s-0040-1707892

Synlett, Table of Contents

Synlett 2020; 31(15): 1482-1486
DOI: 10.1055/s-0040-1707892

letter

Regioselective Synthesis of α-Phosphinoylnaphthols through Rhodium-Catalyzed Annulation of 1-Alkynylphosphine Oxides with Sulfoxonium Ylides

Wucheng Xie ∗

Foshan City Engineering and Technology Research Center for Bioactive Natural Products and Functional Chemicals, School of Environment and Chemical Engineering, Foshan University, #18 Jiang-wan-yi-lu, Chancheng, Foshan, Guangdong, P. R. of China Email: wuchengxie@fosu.edu.cn Email: junjunshi@fosu.edu.cn

,

Binting Lin

,

Xinyi Jian

,

Qinhong Lin

,

Junjun Shi∗

› Author Affiliations

Abstract

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Abstract

α-Phosphinoylnaphthols were obtained by redox-neutral annulation of 1-alkynylphosphine oxides with α-carbonyl sulfoxonium ylides under rhodium(III) catalysis. This protocol shows good regioselectivity and broad functional-group tolerance.

Key words

C–H activation - rhodium catalysis - cyclization - carbocycles - phosphinoylnaphthols - ylides

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References

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16 CCDC 1970775 contains the supplementary crystallographic data for compound 3aa. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
17 4-(Diphenylphosphoryl)-3-phenyl-1-naphthol (3aa); Typical Procedure A Schlenk tube equipped with a stirrer bar was charged with a mixture of diphenyl(phenylethynyl)phosphine oxide (2a, 0.10 mmol), 2-[dimethyl(oxido)-λ⁴-sulfanylidene]-1-phenylethanone (1a, 35.3 mg, 0.18 mmol, 1.8 equiv), [Cp*Rh(CH₃CN)₃](SbF₆)₂ (8.3 mg, 0.01mmol, 10.0 mol%), and Zn(OAc)₂ (5.5 mg, 0.3 equiv). Anhyd DCE (4.0 mL) was added, and the mixture was stirred at 80 °C for 12 h under N₂. The mixture was then concentrated under reduced pressure, and the residue was adsorbed onto a small amount of silica and purified by flash column chromatography [silica gel, EtOAc–CH₂Cl₂ (1:4)] to give a pale-yellow solid; yield: 38.6 mg (92%); mp 278–279 °C. IR (KBr): 3443, 2924, 1584, 1360, 1172, 1148, 1121, 698, 534 cm^–1. ¹H NMR (400 MHz, DMSO): δ = 10.48 (s, 1 H), 8.24 (d, J = 8.2 Hz, 1 H), 7.60–7.54 (m, 1 H), 7.54–7.37 (m, 11 H), 7.20–7.12 (m, 2 H), 7.04 (t, J = 7.6 Hz, 2 H), 6.99–6.89 (m, 3 H). ¹³C NMR (101 MHz, DMSO): δ = 152.13 (d, J = 15.2 Hz), 136.64 (d, J = 5.3 Hz), 136.04 (d, J = 8.2 Hz), 134.39, 134.07 (d, J = 13.1 Hz), 133.37, 131.72, 131.20, 131.11, 129.92, 128.91, 128.22 (d, J = 11.7 Hz), 127.02, 126.82, 126.74, 126.61, 126.35, 125.80 (d, J = 2.0 Hz), 122.04, 110.00 (d, J = 13.4 Hz). ³¹P NMR (162 MHz, DMSO): δ = 26.17. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₈H₂₂O₂P: 421.1352; found: 421.1352.

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