-
2
-
-
0034725770
-
-
Berkowitz, D. B.; Bose, M.; Pfannenstied, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498.
-
(2000)
J. Org. Chem
, vol.65
, pp. 4498
-
-
Berkowitz, D.B.1
Bose, M.2
Pfannenstied, T.J.3
Doukov, T.4
-
4
-
-
33646567717
-
-
Soloshonok, V. A, Ed, American Chemical Society: Washington DC
-
(a) Fuchigami, T.; Tajima, T. In Fluorine-Containing Synthons, ACS Symposium Series 911; Soloshonok, V. A., Ed.; American Chemical Society: Washington DC, 2005, 276.
-
(2005)
Fluorine-Containing Synthons, ACS Symposium Series
, vol.911
, pp. 276
-
-
Fuchigami, T.1
Tajima, T.2
-
5
-
-
34248140027
-
-
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
-
6
-
-
33646400570
-
-
Zagipa, B.; Hidaka, A.; Cao, Y.; Fuchigami, T. J. Fluorine Chem. 2006, 127, 552.
-
(2006)
J. Fluorine Chem
, vol.127
, pp. 552
-
-
Zagipa, B.1
Hidaka, A.2
Cao, Y.3
Fuchigami, T.4
-
7
-
-
27744527559
-
-
Cao, Y.; Hidaka, A.; Tajima, T.; Fuchigami, T. J. Org. Chem. 2005, 70, 9614.
-
(2005)
J. Org. Chem
, vol.70
, pp. 9614
-
-
Cao, Y.1
Hidaka, A.2
Tajima, T.3
Fuchigami, T.4
-
8
-
-
0037012948
-
-
Wnuk, S. F.; Bergolla, L. A.; Garcia, P. I. J. Org. Chem. 2002, 67, 3065.
-
(2002)
J. Org. Chem
, vol.67
, pp. 3065
-
-
Wnuk, S.F.1
Bergolla, L.A.2
Garcia, P.I.3
-
9
-
-
33847799030
-
-
(a) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887.
-
(1976)
J. Am. Chem. Soc
, vol.98
, pp. 4887
-
-
Trost, B.M.1
Salzmann, T.N.2
Hiroi, K.3
-
11
-
-
0029655471
-
-
(a) McCarthy, J. R.; Huber, E. W.; Matthews, L. D. Tetrahedron 1996, 52, 45.
-
(1996)
Tetrahedron
, vol.52
, pp. 45
-
-
McCarthy, J.R.1
Huber, E.W.2
Matthews, L.D.3
-
14
-
-
0000053237
-
-
(a) Fuchigami, T.; Shimojo, M.; Konno, A.; Nakagawa, K. J. Org. Chem. 1990, 55, 6074.
-
(1990)
J. Org. Chem
, vol.55
, pp. 6074
-
-
Fuchigami, T.1
Shimojo, M.2
Konno, A.3
Nakagawa, K.4
-
15
-
-
0032696487
-
-
(b) Dawood, K. M.; Higashiya, S.; Hou, Y.; Fuchigami, T. J. Org. Chem. 1999, 64, 7935.
-
(1999)
J. Org. Chem
, vol.64
, pp. 7935
-
-
Dawood, K.M.1
Higashiya, S.2
Hou, Y.3
Fuchigami, T.4
-
17
-
-
0001202517
-
-
Fuchigami, T.; Shimojo, M.; Konno, A.; Nakagawa, K. J. Org. Chem. 1994, 59, 5937.
-
(1994)
J. Org. Chem
, vol.59
, pp. 5937
-
-
Fuchigami, T.1
Shimojo, M.2
Konno, A.3
Nakagawa, K.4
-
18
-
-
34248227530
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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.
-
-
-
-
25
-
-
0000937513
-
-
Erian, A. W.; Konno, A.; Fuchigami, T. J. Org. Chem. 1995, 60, 7654.
-
(1995)
J. Org. Chem
, vol.60
, pp. 7654
-
-
Erian, A.W.1
Konno, A.2
Fuchigami, T.3
-
27
-
-
0034670617
-
-
Shaaban, M. R.; Ishii, H.; Fuchigami, T. J. Org. Chem. 2000, 65, 8685.
-
(2000)
J. Org. Chem
, vol.65
, pp. 8685
-
-
Shaaban, M.R.1
Ishii, H.2
Fuchigami, T.3
-
28
-
-
34248165362
-
-
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.
-
-
-
|