Copper-catalyzed coupling of aryl iodides and tert-butyl β-keto esters: efficient access to α-aryl ketones and α-arylacetic acid tert-butyl esters

CuI/trans-4-hydroxy-l-proline catalyzed coupling of aryl iodides with tert-butyl β-keto esters proceeded smoothly at 40 °C in DMF, providing α-aryl ketones after acid-promoted deprotection and decarboxylation of tert-butyl ester group. While CuI/2-picolinic acid catalyzed coupling of aryl iodides wi...

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Bibliographic Details
Published in:Tetrahedron 2014-05, Vol.70 (20), p.3327-3332
Main Authors: Zhao, Duo, Jiang, Yongwen, Ma, Dawei
Format: Article
Language:English
Subjects:
Aromatic compounds
Compatibility
Coupling
Coupling (molecular)
Decarboxylation
Esters
Iodides
Ketones
Tetrahedrons
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Summary:CuI/trans-4-hydroxy-l-proline catalyzed coupling of aryl iodides with tert-butyl β-keto esters proceeded smoothly at 40 °C in DMF, providing α-aryl ketones after acid-promoted deprotection and decarboxylation of tert-butyl ester group. While CuI/2-picolinic acid catalyzed coupling of aryl iodides with tert-butyl acetoacetate at 70 °C in dioxane delivered α-arylacetic acid tert-butyl esters upon spontaneous deacylation. A wide range of functional groups, such as acetyl, methoxy, nitrile, nitro, bromo, and chloro were compatible with the reaction conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.10.017