A novel and efficient synthesis of 3-fluorooxindoles from indoles mediated by selectfluor

Organic Letters

Volumn 2, Issue 5, 2000, Pages 639-642

  Takeuchi, Yoshio ^a   Tarui, Takanao ^a   Shibata, Norio ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONIUM COMPOUND; FLUORINE; INDOLE DERIVATIVE; SELECTFLUOR;

ARTICLE; CHEMISTRY; SYNTHESIS;

DIAZONIUM COMPOUNDS; FLUORINE; INDOLES;

EID: 0034624604     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991400y     Document Type: Article

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56. Since Selectfluor seems to decompose slowly in water, 3 equiv of reagent (not 2 equiv) was used when the reaction was performed in aqueous media just in case.
57. 3) δ: 2a -153.7 ppm (q, J = 22.2 Hz); 2b, -159.6 ppm (br dd J = 12.9 Hz, 14.8 Hz); 2c, -153.6 ppm (t, J = 10.2 Hz); 2d, -156.7 ppm (t, J = 14.8 Hz); 2e, -155.3 ppm (t, J = 13.9 Hz); 2f, -157.8 ppm (t, J = 15.7 Hz); 2g, -156.7 ppm (t. J = 14.8 Hz); 2h, -154.8 ppm (t, J = 13.9 Hz); 2i, -152.4 ppm (t, J = 17.8 Hz), -152.6 ppm (t, J = 13.4 Hz); 2j, -154.1 ppm (t. J = 16.6 Hz), -155.0 ppm (br d J = 16.5 Hz); 2k, -156.8 ppm (t, J = 15.7 Hz).
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60. It is of particular interest to note that 3-fluorooxindoles 2 are solely produced in our system, while 3-fluoro-2-methoxyindoline is the product in the reaction of N-tosylindole with Selectfluor. See ref 17b.