Cyclopentadienyl (Cp) ligands are prominent in Rh(III) catalysis. However, there are few studies correlating ligand structure to reactivity. A possible explanation for this void could be the known difficulties for synthesizing cyclopentadienyl ligands. Recent examples reported by our group show cyclopentadienyl ligand development can improve reactivity and selectivity in Rh(III)-catalyzed C-H functionalization reactions. As part of our efforts, we investigate alternative methods for the synthesis of cyclopentadienyl ligands. We identify ring-opening/cross metathesis (ROCM) between 1,2-disubstituted norbornadienes and alkenes as an efficient method for the synthesis of ligand precursors. In the presence of RhCl3 and ethanol, the later can isomerize to give polysubstituted CpRh(III) catalysts. Employing this method allows a rapid access to Rh(III) complexes with different substitution pattern. References (a) Hyster, T. K.; Rovis, T. Chem. Sci. 2011, 2, 1606-1610 (b) Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 11846-11848 (c) Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 2735-2738 (d) Piou, T.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 11292-11295. (e) Hyster, T. K.; Dalton, D. M.; Rovis, T. Chem. Sci. 2015

Efficient synthesis of polysubstituted cyclopentadienyl ligands for Rh(III) catalysis

249th National Meeting (2015)

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