Expedient Synthesis of Terminal Vinylphosphonates by Palladium-Catalyzed C−C Cross-Coupling Reactions of (1-Halovinyl)phosphonates

Yewen Fang; Li Zhang; Xiaoping Jin; Jinjian Li; Meijuan Yuan; Ruifeng Li; Haoqi Gao; Jianghua Fang; Yuyan Liu

doi:10.1055/s-0034-1380326

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(07): 980-984
DOI: 10.1055/s-0034-1380326

letter

Expedient Synthesis of Terminal Vinylphosphonates by Palladium-Catalyzed C−C Cross-Coupling Reactions of (1-Halovinyl)phosphonates

Yewen Fang*

^aSchool of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China eMail: fang@nbut.edu.cn

,

Li Zhang

^bCollege of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China

,

Xiaoping Jin*

^cDepartment of Biology and Pharmaceutical Sciences, Zhejiang Pharmaceutical College, No. 888 Yinxian Avenue East, Ningbo 315100, P. R. of China

,

Jinjian Li

^aSchool of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China eMail: fang@nbut.edu.cn

,

Meijuan Yuan

^bCollege of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China

,

Ruifeng Li*

^bCollege of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China

,

Haoqi Gao

^aSchool of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China eMail: fang@nbut.edu.cn

,

Jianghua Fang

^aSchool of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China eMail: fang@nbut.edu.cn

,

Yuyan Liu

^aSchool of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China eMail: fang@nbut.edu.cn

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Abstract

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Abstract

An efficient new synthetic route to (1-arylvinyl)phosphonates is presented. A wide range of (1-arylvinyl)phosphonates were prepared in good to excellent yields (79–99%) by using a palladium(II) acetate–organophosphine catalyst system. The protocol can be effectively scaled up without deleterious effects. The use of a (1-chlorovinyl)phosphonate as the electrophilic coupling partner was demonstrated for the first time.

Key words

cross-coupling - phosphonates - palladium - catalysis - arylation

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Referenzen

References and Notes

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16 Diethyl [1-(2-Tolyl)vinyl]phosphonate (3b); Typical Procedure A Schlenk flask was charged with phosphonate 2a (97.2 mg, 0.4 mmol), Pd(OAc)₂ (4.5 mg, 0.02 mmol), t-Bu₃P∙HBF₄ (11.6 mg, 0.04 mmol), 2-TolB(OH)₂ (81.6 mg, 0.6 mmol), and K₂CO₃ (138.0 mg, 1.0 mmol). The flask was evacuated for 10 min and then filled with N₂. Toluene (2.0 mL) was added, and the mixture was stirred at r.t. for 10 h. When the reaction as complete, the mixture was diluted with EtOAc (15.0 mL) and the catalyst and inorganic base were removed by filtration through a short pad of silica gel. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography [silica gel, PE–EtOAc (2:1)] to give a pale-yellow oil; yield: 92.5 mg (91%); IR (KBr): 3450, 2983, 2928, 1489, 1392, 1256, 1234, 1022, 962 cm^–1; ¹H NMR (500 MHz, CDCl₃): δ = 1.27 (t, J = 7.0 Hz, 6 H), 2.31 (s, 3 H), 4.04–4.10 (m, 4 H), 5.84 (dd, J = 2.0, 47.7 Hz, 1 H), 6.42 (dd, J = 22.6, 2.0 Hz, 1 H), 7.13–7.17 (m, 2 H), 7.20–7.21 (m, 2 H); ¹³C NMR (125 MHz, CDCl₃): δ = 16.3 (d, J = 6.4 Hz), 20.0, 62.2 (d, J = 6.1 Hz), 125.3 (d, J = 1.5 Hz), 127.8 (d, J = 1.8 Hz), 129.1 (d, J = 3.6 Hz), 130.2, 133.0 (d, J = 8.5 Hz), 136.0 (d, J = 5.4 Hz), 136.6 (d, J = 9.4 Hz), 140.0 (J = 175.8 Hz); ³¹P NMR (202.5 MHz, CDCl₃): δ = 16.0; GC/MS: m/z (%) 254 (27) [M⁺], 226 (11), 197 (48), 179 (5), 144 (4), 115 (100), 91 (12), 65 (8); HRMS (ESI): m/z [M + Na⁺] calcd for C₁₃H₁₉NaO₃P: 277.0970; found: 277.1004.

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