Copper-catalyzed coupling of aryl iodides with aliphatic alcohols

Organic Letters

Volumn 4, Issue 6, 2002, Pages 973-976

  Wolter, Martina ^a   Nordmann, Gero ^a   Job, Gabriel E ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; COPPER; IODIDE;

ARTICLE; CATALYSIS; CHEMISTRY;

ALCOHOLS; CATALYSIS; COPPER; IODIDES;

EID: 0037149634     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025548k     Document Type: Article

References (32)

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28. 3 (1.4-2.0 mmol), aryl iodide (1.0 mmol), and either (a) the alcohol (1 mL) or (b) the alcohol (2 mmol) and toluene (0.5 mL). The test tube was sealed, and the reaction mixture was stirred at 110°C for ∼24 h. The resulting suspension was cooled to room temperature and filtered through a 0.5 × 1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel gave the desired product (see Supporting Information).
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32. To date, allylic alcohols are poor substrates in the analogous Pd-catalyzed couplings. Torraca, K. E.; Huang, X.; Buchwald, S. L. Unpublished results.