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Chemical Communications

Urgent high quality communications from across the chemical sciences.



Hot Article: Cross-coupling with a copper-carbene catalyst


07 November 2008

Avinash Thadani and colleagues from the University of Windsor, in Ontario, have developed a new base metal catalyst that incorporates an N-heterocyclic carbene. The catalyst effectively promotes the reaction between an aromatic halide and ammonia resulting in primary aromatic amines in excellent yields. 

                  A variety of ary and heteroaryl bromides were cross-coupled with ammonia in good to high yields in the presence of a copper-NHC catalyst.

This new catalyst is significant as aromatic amines are important precursors that are used in a variety of industrial processes, such as the production of agrochemicals, polymers and pharmaceuticals. 

Thadani and his team were interested in developing methods for the direct synthesis of amines from ammonia as this would be very cost effective considering ammonia is abundant and cheap. The substrate scope of this methodology is broad and a variety of functional groups are tolerated, indicating the versatility of this system. 

'At present we are currently investigating routes to lower the cost of production of the ligand as well as looking at the possibility of using simpler precursors,' says Thadani. This will reduce the cost of the process and make it much more attractive as an industrial process. 

Thadani explained that 'the ultimate goal would be to manufacture these amines directly from benzene, although there are numerous challenges associated with such an endeavour. Our group has initiated a program to try to address these issues.' 

Michael Brown

Link to journal article

Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst
Rukundo Ntaganda, Bhartesh Dhudshia, Charles L. B. Macdonald and Avinash N. Thadani, Chem. Commun., 2008, 6200
DOI: 10.1039/b815757j