Organic Chemistry Portal



"On Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

Gargi Chakraborti, Sushovan Paladhi, Tirtha Mandal and Jyotirmayee Dash*

*Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India, Email:

G. Chakraborti, S. Paladhi, T. Mandal, J. Dash, J. Org. Chem., 2018, 83, 7347-7359.

DOI: 10.1021/acs.joc.7b03020

see article for more reactions


A CuI-based catalytic system in combination with an easily accessible prolinamide ligand enables an Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides in aqueous media. The method is mild and tolerates air and a wide range of functional groups. Secondary amines like heteroaromatic amines and nucleobases afford the corresponding coupling products in good to excellent yields too.

see article for more examples

Key Words

Ullmann coupling, Arylation, Amination, Green Chemistry

ID: J42-Y2018