Copper(II) catalyzed allylic amination of terpenic chlorides in water
A highly efficient method for the synthesis of allylic amines from terpenic chlorides by cheap copper (II) as catalyst in water has been developed. Allylic chlorides react with high regioselectivity in the presence of secondary amines, under mild conditions to give N-allylic amines in excellent yields.
Graphical abstractVarious terpenic chlorides have been successfully coupled with secondary amines to afford allylic amines in excellent yields. The use of optically active monoterpenes as starting materials allowed preparing terpenic asymmetric amines compounds.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Copper allylic amination of terpenic allylic chlorides. ► Synthesis of terpenic allyl amines with high added value. ► High regioselectivity in the presence of secondary amines. ► Cu(Otf)2 highly active catalyst, commercially available and not air sensitive.
Journal: Catalysis Communications - Volume 19, March 2012, Pages 46–50