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"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: ocjdiacs.res.in

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

DOI: 10.1021/acs.joc.7b03020 (free Supporting Information)


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Abstract

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.

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Key Words

Ullmann coupling, Arylation, Amination, Green Chemistry


ID: J42-Y2018