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Synlett 2018; 29(13): 1729-1734
DOI: 10.1055/s-0037-1610457
DOI: 10.1055/s-0037-1610457
letter
C–H Monoarylation of Naphthylpyrimidines with Aryl Chlorides Catalyzed by a Water-Soluble Ruthenium Complex
This work was supported by the Innovation Scientists and Technicians Troop Construction Projects of Henan Province (154100510015) and the Tackle Key Problems of Science and Technology Project of Henan Province (162102210125).Further Information
Publication History
Received: 01 May 2018
Accepted after revision: 30 May 2018
Publication Date:
10 July 2018 (online)
Abstract
Selective monoarylation of naphthylpyrimidines with a variety of aryl chlorides through C–H bond activation in water was achieved by using a water-soluble [RuCl2-(η6-PhOCH2CH2OH)]2/phosphine catalytic system. The monoarylation occurred at the C-2 carbon of the naphthalene moiety, and selectively polysubstituted naphthylpyrimidines were obtained by a one-pot reaction involving a subsequent hetarylation with 2-pyridyl chlorides.
Key words
ruthenium catalysis - C–H functionalization - arylation - aryl chlorides - naphthylpyrimidines - pyridyl chloridesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610457.
- Supporting Information
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- 23 Substituted Naphthylpyrimidine Derivatives; General Procedure A reaction vessel was charged with the appropriate amount of catalyst A, naphthylpyrimidine (0.5 mmol), aryl chloride (0.6 mmol), K2CO3 (1.5 mmol), RCO2K (0.1 mmol), PAr3 (0.1 mmol), and H2O (3 mL) under N2. The vessel was then sealed and heated at 120 °C (oil-bath temperature) for 24 h. The resulting mixture was cooled to r.t., and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed with H2O, dried (MgSO4), filtered, and concentrated on a rotary evaporator. The resulting residue was purified by flash chromatography. 2-(2-Phenyl-1-naphthyl)pyrimidine (1) White solid; yield: 126 mg (89%). 1H NMR (400 MHz, CDCl3): δ = 8.79 (d, J = 4.9 Hz, 2 H), 8.04 (d, J = 8.5 Hz, 1 H), 7.96 (d, J = 8.0 Hz, 1 H), 7.65 (d, J = 8.5 Hz, 1 H), 7.47–7.58 (m, 3 H), 7.20–7.25 (m, 6 H). 13C NMR (100 MHz, CDCl3): δ = 167.8, 156.8, 141.5, 138.8, 135.2, 132.8, 131.7, 129.5, 129.2, 128.1, 128.0, 127.9, 126.9, 126.6, 125.9, 125.5, 118.8. MS (EI, 70 eV): m/z = 283.1 [M + H]+. Anal. Calcd for C20H14N2: C, 85.08; H, 5.00; N, 9.92. Found: C, 85.32; H, 4.85; N, 9.83.