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7
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38949188144
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General procedure for the non-radioactive fluoroarylation (Table 1, Column 2): To a solution of the substrate (4 mmol) in aqueous titanium(III) chloride (3 mL, ca. 1 M solution in dilute hydrochloric acid, ca. 3.0 mmol) 4-fluorobenzenediazonium tetrafluoroborate (209 mg, 1.0 mmol) was added in one batch. The resulting solution was stirred under argon at 45 °C for 20 min and diluted with water (5 mL). After the careful addition of satd aqueous sodium carbonate (30 mL) the mixture was extracted with ether (3 × 20 mL). The combined extracts were dried over sodium sulfate and concentrated. Purification was achieved by column chromatography.
-
General procedure for the non-radioactive fluoroarylation (Table 1, Column 2): To a solution of the substrate (4 mmol) in aqueous titanium(III) chloride (3 mL, ca. 1 M solution in dilute hydrochloric acid, ca. 3.0 mmol) 4-fluorobenzenediazonium tetrafluoroborate (209 mg, 1.0 mmol) was added in one batch. The resulting solution was stirred under argon at 45 °C for 20 min and diluted with water (5 mL). After the careful addition of satd aqueous sodium carbonate (30 mL) the mixture was extracted with ether (3 × 20 mL). The combined extracts were dried over sodium sulfate and concentrated. Purification was achieved by column chromatography.
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8
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38949172284
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For a first synthesis of stilbenes from arenediazonium salts, see:
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For a first synthesis of stilbenes from arenediazonium salts, see:. Obushak N.D., Lyakhovich M.B., Ganushchak N.I., and Bilaya E.E. J. Org. Chem. USSR 19 (1983) 1391-1392
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(1983)
J. Org. Chem. USSR
, vol.19
, pp. 1391-1392
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Obushak, N.D.1
Lyakhovich, M.B.2
Ganushchak, N.I.3
Bilaya, E.E.4
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9
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33646459933
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For a recent synthesis of paroxetine, see:
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For a recent synthesis of paroxetine, see:. Pastre J.C., and Correia R.D. Org. Lett. 8 (2006) 1657-1660
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(2006)
Org. Lett.
, vol.8
, pp. 1657-1660
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Pastre, J.C.1
Correia, R.D.2
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10
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9744219625
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For binding properties of 3-aryltropane derivatives to monamine transporters, see:
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For binding properties of 3-aryltropane derivatives to monamine transporters, see:. Carroll F.I., Runyon S.P., Abraham P., Navarro H., Kuhar M.J., Pollard G.T., and Howard J.L. J. Med. Chem. 47 (2004) 6401-6409
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(2004)
J. Med. Chem.
, vol.47
, pp. 6401-6409
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Carroll, F.I.1
Runyon, S.P.2
Abraham, P.3
Navarro, H.4
Kuhar, M.J.5
Pollard, G.T.6
Howard, J.L.7
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11
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0029824217
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Holmquist C.R., Keverline-Frantz K.I., Abraham P., Boja J.W., Kuhar M.J., and Carroll F.I. J. Med. Chem. 39 (1996) 4139-4141
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(1996)
J. Med. Chem.
, vol.39
, pp. 4139-4141
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Holmquist, C.R.1
Keverline-Frantz, K.I.2
Abraham, P.3
Boja, J.W.4
Kuhar, M.J.5
Carroll, F.I.6
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12
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38949145215
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note
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The degree of hydrogen abstraction by the aryl radical cannot easily be determined in experiments with fluorobenzenediazonium salts due to the volatility of fluorobenzene. An attempt with 4-methoxybenzenediazonium tetrafluoroborate and arecoline under standard conditions (see Ref. 8) gave 46% of the desired adduct along with 35% of anisole.
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13
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0035915387
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Kung H.F., Lee C.W., Zhuang Z.P., Kung M.P., Hou C., and Plossl K. J. Am. Chem. Soc. 123 (2001) 12740-12741
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(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 12740-12741
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Kung, H.F.1
Lee, C.W.2
Zhuang, Z.P.3
Kung, M.P.4
Hou, C.5
Plossl, K.6
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14
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0023732093
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2O target with an 11-MeV proton beam at the in-house RDS-112 cyclotron (Siemens/CTI)
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2O target with an 11-MeV proton beam at the in-house RDS-112 cyclotron (Siemens/CTI). Feliu A.J. J. Labelled Compd. Radiopharm. 25 (1988) 1245-1253
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(1988)
J. Labelled Compd. Radiopharm.
, vol.25
, pp. 1245-1253
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Feliu, A.J.1
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16
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38949192759
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note
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3CN. The following gradient was used for 5 and 6: 0 min 5% B, 8 min 40%. For 7 as the gradient was used 0 min 10% B, 8 min 50% B (for further details see Supplementary data).
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17
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38949174133
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note
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Highest radiochemical yields were obtained using a relatively high precursor amount of 50 mg. However, good radiochemical yields ≥50% can also be achieved using smaller precursor amounts. A radiochemical yield of 54% was obtained within 5 min using 10 mg of bromostyrene 4b.
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