Simple Catalytic Mechanism for the Direct Coupling of 伪-Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix

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• 作者：Ryan W. Evans ; Jason R. Zbieg ; Shaolin Zhu ; Wei Li ; David W. C. MacMillan
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：October 30, 2013
• 年：2013
• 卷：135
• 期：43
• 页码：16074-16077
• 全文大小：301K
• 年卷期：v.135,no.43(October 30, 2013)
• ISSN：1520-5126

文摘

The direct 伪-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful 伪-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated 伪-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the 伪-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.