Issue 3, 2014

Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis

Abstract

A single set of conditions consisting of a palladium catalyst, a commercially available ligand, and a base, allow for several types of C–N bond constructions to be conducted in water with the aid of a commercially available “designer” surfactant (TPGS-750-M). Products containing a protected NH2 group in the form of a carbamate, sulfonamide, or urea can be fashioned starting with aryl or heteroaryl bromides, iodides, and in some cases, chlorides, as substrates. Reaction temperatures are in the range of room temperature to, at most, 50 °C, and result in essentially full conversion and good isolated yields.

Graphical abstract: Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis

Supplementary files

Article information

Article type
Paper
Submitted
23 Oct 2013
Accepted
13 Dec 2013
First published
02 Jan 2014

Green Chem., 2014,16, 1480-1488

Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis

N. A. Isley, S. Dobarco and B. H. Lipshutz, Green Chem., 2014, 16, 1480 DOI: 10.1039/C3GC42188K

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