Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands
A series of imidazolium salts precursors for N-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrO...
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| Main Authors: | , , |
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| Format: | Article |
| Published: |
Royal Society of Chemistry
2019
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| Subjects: | |
| Online Access: | http://eprints.utm.my/id/eprint/87744/ http://dx.doi.org/10.1039/c9dt01219b |
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| Institution: | Universiti Teknologi Malaysia |
| Summary: | A series of imidazolium salts precursors for N-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrOH shows that the rhodium complexes bearing fluorinated NHCs are better than their non-fluorinated counterparts. The order of activity being 4-F-C6H4 < 2,4-F2-C6H3 < 2,4,5-F3-C6H2 < 2,6-F2-C6H3 < 2,4,6-F3-C6H2. This order of reactivity is consistent with a number of simple NMR measures of the electronic properties of these systems, including 1JCH of the NHC·HBF4 salts, δ(77Se) of the NHC selenides and 1JRh-C and δ(13Ccarbene) of the [Rh(cod)Cl(NHC)] complexes. |
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