Iodination of organotrifluoroborates: Synthesis of vinyl and alkynyl iodides

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1417-1419

  Kabalka, George W ^a   Mereddy, Arjun Reddy ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

Alkynyl iodides; Iodination; Organotrifluoroborates; Vinyl iodides

Indexed keywords

ALKYNYL GROUP; BORIC ACID; FLUORINE DERIVATIVE; IODINE DERIVATIVE; SODIUM IODIDE; TOSYLCHLORAMIDE SODIUM; VINYL DERIVATIVE;

ARTICLE; IODINATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 1642538440     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.050     Document Type: Article

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32. General procedure: To a solution of potassium vinyl- or alkynyltrifluoroborate (1.00 mmol) in 50% aqueous tetrahydrofuran (5 mL) contained in a round bottomed flask (which was shielded from light), chloramine-T (1.00 mmol) was added followed by sodium iodide (1.05 mmol). The resulting mixture was stirred at room temperature for the required length of time (Tables 1 and 2). After the reaction was complete, 10% aqueous sodium thiosulfate (2 mL) was added to decompose excess iodine. The mixture was extracted with ethyl acetate (3 × 25 mL), the combined organic extracts washed with water (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified by column chromatography using silica gel (100-200 mesh) and petroleum ether/ethyl acetate as eluent (98:2). The products were identified by comparison of the physical and spectral properties with literature values.