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Chemical Communications

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Hot article: P,N-heterocyclic carbenes


18 September 2008

Guy Bertrand and colleagues from the University of California, Riverside, have synthesised cyclic (amino)(phosphino)carbenes (P-NHCs), and observed during their deprotonation the formation of a metastable P-NHC, an azomethine ylide, and a bicyclic phosphirane. 

 

Conjugate acids of cyclic (amino)(phosphino)carbenes have been prepared, and several different processes have been observed during their deprotonation

 

'Any catalytic application requiring electron rich ligands might benefit from the use of P-NHC ligands', says Bertrand. 'Recently, spectacular results have been achieved in the area of homogeneous catalysis using cyclic diaminocarbene ligands, and this is mainly because of their strong sigma-donor and weak pi-acceptor properties. Heavier elements (such as phosphorus) have inherent pi-donor capabilities that are either as large or larger than their second row counterparts (such as nitrogen). The P-NHCs are therefore very interesting candidates as ligands for transition metal catalysts.' 

The next challenge the scientists face is finding the right set of substituents to isolate P-NHCs at room temperature, and make them easier to handle. 

Rachel Cooper

Link to journal article

A persistent P,N-heterocyclic carbene
Guido D. Frey, Maoying Song, Jean-Baptiste Bourg, Bruno Donnadieu, Michele Soleilhavoup and Guy Bertrand, Chem. Commun., 2008, 4711
DOI: 10.1039/b812333k