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Cu-Catalyzed Double C(sp3)-H Functionalization of Ethylarenes to Form Arylethanolamines
Naoki Oku1,2, Tomoya Miura2
1Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Abstract:
A double C(sp3)-H functionalization of ethylarenes with alcohols and N-fluorobenzenesulfonimide is reported. The reaction proceeds in three stages. (1) Cu-catalyzed benzylic alkoxylation of ethylarenes gives 1-(1-alkoxyethyl)benzenes. (2) The resulting 1-(1-alkoxyethyl)benzenes are gradually converted into vinylarenes. (3) Cu-catalyzed aminoalkoxylation of the intermediary vinylarenes yields arylethanolamines. Overall, the C-N and C-O bonds are introduced regioselectively at the homobenzylic and benzylic positions of ethylarenes.
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