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Acetone Cyanohydrin as a Source of HCN in the Cu-Catalyzed Hydrocyanation of α-Aryl Diazoacetates

Eun Ju Park, Seungeon Lee and Sukbok Chang*

*Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Republic of Korea, Email: sbchangkaist.ac.kr

E. J. Park, S. Lee, S. Chang, J. Org. Chem., 2010, 75, 2760-2762.

DOI: 10.1021/jo100356d (free Supporting Information)


Abstract

A procedure for a Cu-catalyzed hydrocyanation of α-aryl diazoesters using acetone cyanohydrin as a source of hydrogen cyanide is significantly accelerated by addition of trimethylsilyl cyanide (TMSCN) presumably by delivering free cyanide ion in situ. This method provides various types of α-aryl cyanoacetates in good yields under mild conditions.

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Key Words

Nitriles


ID: J42-Y2010-1100