C–H Monoarylation of Naphthylpyrimidines with Aryl Chlorides Catalyzed by a Water-Soluble Ruthenium Complex

Hong-Mei Li; Tian-Yong Tu; Xin Han; Zhi-Qiang Wang; Wei-Jun Fu; Xin-Qi Hao; Mao-Ping Song; Chen Xu

doi:10.1055/s-0037-1610457

Synlett, Table of Contents

Synlett 2018; 29(13): 1729-1734
DOI: 10.1055/s-0037-1610457

letter

C–H Monoarylation of Naphthylpyrimidines with Aryl Chlorides Catalyzed by a Water-Soluble Ruthenium Complex

Hong-Mei Li

^aCollege of Chemistry and Chemical Engineering, and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471022, P. R. of China Email: wzq197811@163.com

,

Tian-Yong Tu

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, P. R. of China Email: xqhao@zzu.edu.cn

,

Xin Han

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, P. R. of China Email: xqhao@zzu.edu.cn

,

Zhi-Qiang Wang*

^aCollege of Chemistry and Chemical Engineering, and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471022, P. R. of China Email: wzq197811@163.com

,

Wei-Jun Fu

^aCollege of Chemistry and Chemical Engineering, and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471022, P. R. of China Email: wzq197811@163.com

,

Xin-Qi Hao*

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, P. R. of China Email: xqhao@zzu.edu.cn

,

Mao-Ping Song

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, P. R. of China Email: xqhao@zzu.edu.cn

,

Chen Xu*

^aCollege of Chemistry and Chemical Engineering, and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471022, P. R. of China Email: wzq197811@163.com

^cCollege of Food and Pharmacy, Luoyang Normal University, Luoyang 471022, P. R. of China Email: xubohan@163.com

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Abstract

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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 chlorides

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References

References and Notes

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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.

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