메뉴 건너뛰기




Volumn , Issue 7, 2007, Pages 1148-1152

Regioselective anodic fluorination of α-(arylthio)benzylphosphonate esters, α-(arylthio)methylphosphonate esters and their analogues

Author keywords

fluorophosphonate ester; Anodic substitution; Electrochemical fluorination; Electrosynthesis; Emmons Wittig reagent

Indexed keywords

ALPHA ARYLTHIOBENZYLPHOSPHONATE ESTER DERIVATIVE; ALPHA ARYLTHIOMETHYLPHOSPHONATE ESTER DERIVATIVE; ALPHA FLUOROPHOSPHONATE ESTER DERIVATIVE; DIETHYL ALPHA FLUORO ALPHA (2 PYRIDYLTHIO)BENZYLPHOSPHONATE; DIETHYL ALPHA FLUORO ALPHA (4 PYRIDYLTHIO)BENZYLPHOSPHONATE; DIETHYL ALPHA FLUORO ALPHA PHENYLTHIO 4 IODEBENZYLPHOSPHONATE; DIETHYL ALPHA FLUORO ALPHA PHENYLTHIO 4 METHOXYBENZYLPHOSPHONATE; DIETHYL ALPHA FLUORO ALPHA PHENYLTHIOBENZYLPHOSPHONATE; DIETHYL FLUORO (2 NAPHTHYLPHENYLTHIO)METHYLPHOSPHONATE; DIMETHOXYETHANE; ESTER DERIVATIVE; ETHANE; NITROMETHANE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34248229133     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977439     Document Type: Article
Times cited : (12)

References (29)
  • 5
    • 34248140027 scopus 로고    scopus 로고
    • 4th ed, Lund, H, Hammerich, O, Eds, Marcel Dekker: New York, Chap. 25
    • (b) Fuchigami, T. Organic Electrochemistry, 4th ed.; Lund, H.; Hammerich, O., Eds.; Marcel Dekker: New York, 2001, Chap. 25.
    • (2001) Organic Electrochemistry
    • Fuchigami, T.1
  • 18
    • 34248227530 scopus 로고    scopus 로고
    • 2) was passed until the starting material 1 was almost consumed (monitored by TLC). After electrolysis, the electrolytic solution was passed through a short column filled with silica gel using EtOAc as an eluent to remove fluoride salts. The eluent was evaporated under reduced pressure, and the residue was further purified by column chromatography on silica gel using EtOAc to give pure fluorinated products. The products were identified by spectroscopic data.
    • 2) was passed until the starting material 1 was almost consumed (monitored by TLC). After electrolysis, the electrolytic solution was passed through a short column filled with silica gel using EtOAc as an eluent to remove fluoride salts. The eluent was evaporated under reduced pressure, and the residue was further purified by column chromatography on silica gel using EtOAc to give pure fluorinated products. The products were identified by spectroscopic data.
  • 19
    • 34248142067 scopus 로고    scopus 로고
    • Diethyl α-Fluoro-α-(phenylthio)benzylphosphonate (2a, 1H NMR (CDCl3, δ, 1.11 (t, J, 7.09 Hz, 3 H, 1.31 (t, J, 7.09 Hz, 3 H, 3.69-3.79 (m, 1 H, 3.91-4.02 (m, 1 H, 4.05-4.22 (m, 2 H, 7.13-7.55 (m, 10 H, 13C NMR (CDCl3, δ, 16.3 (d, JPC, 11.7 Hz, 16.4 (d, J PC, 11.7 Hz, 64.4 (dd, JFC, 0.02 Hz, JPC, 7.27 Hz, 64.6 (dd, JFC, 0.02 Hz, JPC, 7.27 Hz, 106.2 (dd, JPC, 175.7 Hz, JFC, 234.3 Hz, 126.3 (t, J, 3.91 Hz, 126.4 (t, J, 3.91 Hz, 127.7 (t, JPC, JFC, 1.68 Hz, 128.3, 128.7 (d, J, 1.68 Hz, 129.0, 134.8 (d, J, 22.4 Hz, 135.9 (d, J, 2.24 Hz, 19F NMR (CDCl3, δ, 67.3 d, JPF, 90.4 Hz, HRMS: m/z calcd for
    • 3PS: 354.0855; found: 354.0843.
  • 20
    • 34248177706 scopus 로고    scopus 로고
    • Diethyl α-Fluoro-α-(phenylthio)-4-methoxybenzylphosphonate (6, 1H NMR (CDCl3, δ, 1.14 (t, J, 6.75 Hz, 3 H, 1.32 (t, J, 6.75 Hz, 3 H, 3.80 (s, 3 H, 3.91-3.97 (m, 1 H, 4.07-4.19 (m, 1 H, 4.29-4.33 (m, 2 H, 6.83 (d, J, 8.64 Hz, 2 H, 7.36-7.58 (m, 5 H, 7.63 (d, J, 7.83 Hz, 2 H, 13C NMR (CDCl3, δ, 16.1 (d, JPC, 5.56 Hz, 16.3 (d, JPC, 5.56 Hz, 64.6 (dd, JFC, 1.68 Hz, JPC, 7.25 Hz, 65.2 (d, JPC, 6.70 Hz, 106.4 (dd, JPC, 162.3 Hz, JFC, 229.2 Hz, 113.4 (t, JPC, JFC, 1.68 Hz, 113.6 (t, JPC, JFC, 1.68 Hz, 127.7 (d, JPC, 3.35 Hz, 127.8 (d, JPC, 3.35 Hz, 130.4, 134.1, 134.5 (d, J, 2.80 Hz, 160.6; 19F NMR CDC
    • 6PS: 416.0859; found: 416.0862.
  • 21
    • 34248224059 scopus 로고    scopus 로고
    • Diethyl α-Fluoro-α-(phenylthio)-4- iodebenzylphosphonate (7, 1H NMR (CDCl3, δ, 1.09 (t, J, 7.09 Hz, 3 H, 1.29 (t, J, 7.09 Hz, 3 H, 3.69-3.78 (m, 1 H, 3.93-4.01 (m, 1 H, 4.09-4.22 (m, 2 H, 7.13-7.25 (m, 5 H, 7.40 (d, J, 7.03 Hz, 2 H, 7.54 (d, J, 7.03 Hz, 2 H, 13C NMR (CDCl3, δ, 16.2 (d, JFC, 11.7 Hz, 16.4 (d, JPC, 11.7 Hz, 64.3 (dd, JFC, 1.68 Hz, JPC, 7.27 Hz, 64.6 (dd, JFC, 1.68 Hz, JPC, 7.27 Hz, 106.0 (dd, JPC, 174.6 Hz, JFC, 233.7 Hz, 126.3 (t, JPC, JFC, 7.83 Hz, 126.4 (t, JPC, JFC, 7.83 Hz, 127.7 (t, JPC, JFC, 1.68 Hz, 128.3, 128.6 (d, J, 7.83 Hz, 129.0, 134.9 (d, J, 22.9 Hz, 135.8 d
    • 3PS: 479.9821; found: 479.9809.
  • 22
    • 34248194175 scopus 로고    scopus 로고
    • Diethyl [Fluoro(2-naphthyl)(phenylthio)methyl]phosphonate (8, 1H NMR (CDCl3, δ, 1.07 (t, J, 7.02 Hz, 3 H, 1.28 (t, J, 7.02 Hz, 3 H, 3.65-3.78 (m, 1 H, 3.91-4.04 (m, 1 H, 4.12-4.25 (m, 2 H, 7.07-7.16 (m, 3 H, 7.41-7.47 (m, 4 H, 7.47-7.79 (m, 4 H, 7.94 (m, 1 H, 13C NMR (CDCl3, δ, 16.3 (d, JPC, 5.56 Hz, 16.4 (d, JPC, 5.56 Hz, 64.5 (d, JPC, 7.26 Hz, 65.2 (d, JPC, 7.26 Hz, 106.2 (dd, JPC, 176.8 Hz, JFC, 234.3 Hz, 124.0 (dd, JPC, 2.80 Hz, JFC, 5.59 Hz, 125.8 (dd, JPC, 5.59 Hz, JFC, 9.50 Hz, 126.1, 126.5, 127.4, d, JFC, 6.10 Hz, 128.4, 128.5, 128.8, 132.4 (t, JFC, 11.1 Hz, 132.8, 135.8; 19F NMR (CDCl3, δ, 65.9 d, JPF, 92.5 H
    • 3PS: 404.1011; found: 404.1007.
  • 23
    • 34248145888 scopus 로고    scopus 로고
    • Diethyl α-Fluoro-α-(2-pyridylthio)benzylphosphonate (11, 1H NMR (CDCl3, δ, 1.14 (t, J, 7.02 Hz, 3 H, 1.26 (t, J, 7.02 Hz, 3 H, 3.89 (q, J, 7.29 Hz, 1 H, 4.14 (q, J, 6.48 Hz, 1 H, 4.34 (q, J, 6.9 Hz, 2 H, 6.90-7.56 (m, 8 H, 8.34 (d, J, 4.86 Hz, 1 H, 13C NMR (CDCl3, δ, 16.33 (d, JPC, 10.62 Hz, 16.39 (d, JPC, 10.65 Hz, 64.7 (dd, JPC, 7.29 Hz, JFC, 31.02 Hz, 65.1 (dd, JPC, 6.78 Hz, JFC, 22.87 Hz, 106.21 (dd, JPC, 170.11 Hz, JFC, 230.11 Hz, 126,3 (t, JPC, 3.91 Hz, 126.6 (t, JPC, 3.91 Hz, 127.9 (s, 128.2 (t, J, 1.69 Hz, 129.1 (t, J, 1.68 Hz, 134.5 (d, J, 22.42 Hz, 149.19 (s, 19F NMR (CDCl3, δ, 66.28 d
    • 3PS: 355.0807; found: 355.0800.
  • 24
    • 34248169566 scopus 로고    scopus 로고
    • Diethyl α-Fluoro-α-(4-pyridylthio)benzylphosphonate (12, 1H NMR (CDCl3, δ, 1.13 (t, J, 7.02 Hz, 3 H, 1.29 (t, J, 7.02 Hz, 3 H, 3.86 (q, J, 7.29 Hz, 1 H, 4.01 (q, J, 7.02 Hz, 1 H, 4.15 (q, J, 6.95 Hz, 2 H, 7.16-7.53 (m, 5 H, 7.57 (d, J, 6.92 Hz, 2 H, 8.34 (d, J, 5.21 Hz, 2 H, 13C NMR (CDCl3, δ, 16.30 (d, JPC, 10.62 Hz, 16.38 (d, JPC, 10.62 Hz, 64.76 (dd, JPC, 7.25 Hz, JFC, 22.85 Hz, 65.1 (dd, JPC, 6.71 Hz, JFC, 22.31 Hz, 106.1 (dd, JPC, 169.52 Hz, JFC, 229.8 Hz, 126,3 (t, JPC, 3.91 Hz, 126.6 (t, JPC, 3.91 Hz, 127.6 (s, 128.1 (t, J= 1.68 Hz, 128.9 (t, J, 1.68 Hz, 134.1 (d, J, 22.36 Hz, 149.17 (s, 19F NMR CDCl
    • 3PS: 355.0807; found: 355.0789.
  • 28
    • 34248165362 scopus 로고    scopus 로고
    • Diethyl [Fluoro(4-pyridylthio)methyl]phosphonate (19, 1H NMR (CDCl3, δ, 1.37 (t, J, 7.09 Hz, 6 H, 4.24-4.36 (m, 4 H, 6.19 (dd, JHF, 53.6 Hz, J HP, 7.56 Hz, 1 H, CHF, 7.34 (d, J, 1.48 Hz, 1 H, 7.36 (d, J, 1.48 Hz, 1 H, 8.53 (d, J, 1.48 Hz, 1 H, 8.55 (d, J, 1.48 Hz, 1 H, 13C NMR (CDCl3, δ, 16.65 (d, JPC, 6.15 Hz, 64.5 (dd, JPC, 6.70 Hz, JFC, 11.7 Hz, 93.7 (dd, JPC, 177.2 Hz, JFC, 232.5 Hz, CHF, 122.9 (d, JFC, 1.68 Hz, 144.5 (d, JPC, 2.80 Hz, 144.7 (d, JPC, 2.80 Hz, 149.9 (s, 19F NMR (CDCl3, δ, 93.6 dd, JPF, 83.3 Hz, JHF, 53.6 Hz, HRMS: m/z calcd for C10H15FNQ3PS: 279.0494;
    • 3PS: 279.0494; found: 279.0489.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.