Tunable, Chemoselective Amination via Silver Catalysis

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• 作者：Jared W. Rigoli ; Cale D. Weatherly ; Juliet M. Alderson ; Brian T. Vo ; Jennifer M. Schomaker
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：November 20, 2013
• 年：2013
• 卷：135
• 期：46
• 页码：17238-17241
• 全文大小：411K
• 年卷期：v.135,no.46(November 20, 2013)
• ISSN：1520-5126

文摘

Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C鈥揌 bond or add it directly to a C鈺怌 bond. However, it has been challenging to develop well-defined catalysts capable of promoting predictable and chemoselective aminations solely through reagent control. Herein, we report remarkable chemoselective aminations that employ a single metal (Ag) and a single ligand (phenanthroline) to promote either aziridination or C鈥揌 insertion by manipulating the coordination geometry of the active catalysts.