Thermal and microwave hydrolysis of organotrifluoroborates mediated by alumina

Tetrahedron Letters

Volumn 50, Issue 46, 2009, Pages 6271-6272

  Kabalka, George W ^a   Coltuclu, Vitali ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM OXIDE; BORIC ACID; REAGENT;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; MICROWAVE RADIATION; THERMAL ANALYSIS;

EID: 70349501341     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.008     Document Type: Article

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28. Interestingly, LiOH was ineffective for hydrolyzing organotrifluoroborates under our reaction conditions.
29. 3 contained in a 25 mL round-bottomed flask. The resulting suspension was inserted into a CEM Discover microwave unit and stirred for 15 min at 70 °C. The mixture was extracted with ethyl acetate (3 × 10 mL), the extracts combined, dried over anhydrous sodium sulfate, filtered, and the solvent evaporated to yield 4-formylphenylboronic acid as a white solid (134 mg, 92%).
30. The procedure paralleled that described in Ref. 9 except that the stirred mixture was heated in an oil bath at 70 °C for a period of 30 min.
31. During the review process, we were made aware of a new hydrolysis procedure developed by Molander and his group {Journal of Organic Chemistry, ASAP}.