Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

“On Water’’ Promoted Ullmann-Type C–N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols
Tirtha Mandal, Sushovan Paladhi, Gargi Chakraborti, Jyotirmayee Dash
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b03020

DOI: 10.1021/acs.joc.7b03020

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