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Issue 3, 2014
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Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis

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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

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Publication details

The article was received on 23 Oct 2013, accepted on 13 Dec 2013 and first published on 02 Jan 2014


Article type: Paper
DOI: 10.1039/C3GC42188K
Citation: Green Chem., 2014,16, 1480-1488
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    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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