m-Iodosylbenzoic acid, a tagged hypervalent iodine reagent for the iodo-functionalization of alkenes and alkynes

Tetrahedron Letters

Volumn 49, Issue 9, 2008, Pages 1506-1509

  Yusubov, Mekhman S ^a   Yusubova, Roza Ya ^a   Kirschning, Andreas ^b   Park, Joo Yeon ^c   Chi, Ki Whan ^c  

^a SIBERIAN STATE MEDICAL UNIVERSITY   (Russian Federation)

^b LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^c University of Ulsan   (South Korea)

Author keywords

Alkenes; Alkynes; Hypervalent iodine; Iodination; m Iodosobenzoic acid; Scavenger

Indexed keywords

2 IODOBENZOIC ACID; 2 IODOSYLBENZOIC ACID; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ANION EXCHANGE RESIN; BENZOIC ACID DERIVATIVE; HYDROCHLORIC ACID; IODINE; IODINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ACIDIFICATION; ARTICLE; HYDROXYLATION; ISOLATION PROCEDURE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 38749083005     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.120     Document Type: Article

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58. 2O (5:1, 0.5 mL) was employed as solvent instead of MeOH. Typical procedure for diiododimethoxylation. To a solution of iodine (28 mg, 0.11 mmol) and m-iodosylbenzoic acid (2) (29 mg, 0.11 mmol) in MeOH (0.5 mL) were added alkynes 6a-f (0.15 mmol) in MeOH (0.5 mL), and the reaction mixture was stirred at room temperature for 1 h. Then, dichloromethane (1.0 mL) was added and the resulting solution was cooled to 5 °C. IRA 900 (350-400 mg, hydroxide form) was added and the mixture was stirred for 5 min in the dark. The resin was removed by filtration and the solution was concentrated under reduced pressure to afford pure diiodoketals 9a-f as judged by NMR-spectroscopy.
59. 2: C, 30.58; H, 3.27. Found: C, 30.71; H, 3.59.