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Synlett 2020; 31(15): 1482-1486
DOI: 10.1055/s-0040-1707892
DOI: 10.1055/s-0040-1707892
letter
Regioselective Synthesis of α-Phosphinoylnaphthols through Rhodium-Catalyzed Annulation of 1-Alkynylphosphine Oxides with Sulfoxonium Ylides
Funding from the Natural Science Foundation of Guangdong Province (2017A030310577, 2018A030310351) and the Foundation for Distinguished Young Talents in Higher Education of Guangdong (2017KQNCX211) is gratefully acknowledged.Further Information
Publication History
Received: 25 April 2020
Accepted after revision: 21 May 2020
Publication Date:
23 June 2020 (online)
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 - ylidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707892.
- Supporting Information
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- 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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