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Volumn 49, Issue 11, 2008, Pages 1881-1883

Radical fluoroarylation in radiochemical synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ARECOLINE; FLUOROBENZENE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RADIOPHARMACEUTICAL AGENT; STILBENE DERIVATIVE; STYRENE DERIVATIVE;

EID: 38949151586     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.128     Document Type: Article
Times cited : (10)

References (18)
  • 7
    • 38949188144 scopus 로고    scopus 로고
    • 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.
  • 9
    • 33646459933 scopus 로고    scopus 로고
    • For a recent synthesis of paroxetine, see:
    • For a recent synthesis of paroxetine, see:. Pastre J.C., and Correia R.D. Org. Lett. 8 (2006) 1657-1660
    • (2006) Org. Lett. , vol.8 , pp. 1657-1660
    • Pastre, J.C.1    Correia, R.D.2
  • 12
    • 38949145215 scopus 로고    scopus 로고
    • note
    • 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.
  • 14
    • 0023732093 scopus 로고
    • 2O target with an 11-MeV proton beam at the in-house RDS-112 cyclotron (Siemens/CTI)
    • 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
    • (1988) J. Labelled Compd. Radiopharm. , vol.25 , pp. 1245-1253
    • Feliu, A.J.1
  • 16
    • 38949192759 scopus 로고    scopus 로고
    • note
    • 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).
  • 17
    • 38949174133 scopus 로고    scopus 로고
    • note
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.