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A three-component amino etherification of alkenes presents an ideal and direct strategy to access high-value 1,2-alkylamino ethers, yet it remains challenging. Herein, we disclose a catalytic three-component amino etherification of alkenes that enables the unprecedented incorporation of versatile aliphatic amines and structurally diverse alkyl or aryl ethers onto alkenes with various substitution patterns. The success of this method relies on a copper-catalyzed electrophilic amination of alkenes using O -benzoyl hydroxylamines and the subsequent C–O bond formation using silyl ethers. Mechanistic studies further reveal the critical role of silyl ethers in alkoxide transmetalation during the C–O coupling step, which guided us in the development of a more convenient protocol for amino oxygenation of alkenes directly using alcohols and phenols with in situ silyl ether formation. This catalytic method has been successfully applied to the functionalization of a wide range of complex bioactive molecules, such as terpenoids, amino acids, nucleobases, and various heterocycles, showing broad functional group compatibility and great potential for applications in synthetic and medicinal chemistry.
Feng et al. (Fri,) studied this question.