Chakraborti Gargi, Paladhi Sushovan, Mandal Tirtha, Dash Jyotirmayee
Department of Organic Chemistry , Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032 , India.
J Org Chem. 2018 Jul 20;83(14):7347-7359. doi: 10.1021/acs.joc.7b03020. Epub 2018 Feb 15.
The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.
报道了在水介质中使用基于碘化亚铜的催化体系与易于获得的脯氨酰胺配体相结合，实现各种芳香族、脂肪族胺与芳基卤化物的乌尔曼型交叉偶联。该方法温和，对空气、水分和多种官能团具有耐受性，为获得各种胺化产物提供了一种新方法。也使用了诸如杂芳族胺和核碱基之类的仲胺，以良好至优异的产率得到相应的偶联产物。此外，该方法已用于氨基酚的化学选择性C-N芳基化，并进一步用于咔唑天然产物的合成，避免了保护和脱保护步骤。
