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Practically convenient and industrially-aligned methods for iridium-catalysed hydrogen isotope exchange processes

Cochrane, A R and Idziak, C and Kerr, William and Mondal, Bhaskar and Paterson, Laura C and Tuttle, Tell and Andersson, S. and Nilsson, G.N. (2014) Practically convenient and industrially-aligned methods for iridium-catalysed hydrogen isotope exchange processes. Organic and Biomolecular Chemistry, 12 (22). pp. 3598-3603. ISSN 1477-0520

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Abstract

The use of alternative solvents in the iridium-catalysed hydrogen isotope exchange reaction with developing phosphine/NHC Ir(I) complexes has identified reaction media which are more widely applicable and industrially acceptable than the commonly employed chlorinated solvent, dichloromethane. Deuterium incorporation into a variety of substrates has proceeded to deliver high levels of labelling (and regioselectivity) in the presence of low catalyst loadings and over short reaction times. The preparative outputs have been complemented by DFT studies to explore ligand orientation, as well as solvent and substrate binding energies within the catalyst system.