Chemistry - A European Journal p. 10729 - 10734 (2020)
Update date:2022-07-30
Topics: Regioselectivity Column chromatography Yield NMR spectroscopy Mass spectrometry (MS) Cyclization TLC (thin-layer chromatography) Reductive Elimination Substrate Scope Ligand Exchange Oxidative Coupling C–H Activation Isoindolinones RhIII-catalyzed
Shaaban, Saad
Davies, Caitlin
Merten, Christian
Flegel, Jana
Otte, Felix
Strohmann, Carsten
Waldmann, Herbert
RhIII-catalyzed C?H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho-substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigations support that the high regioselectivity observed for these substrates results from the presence of an ortho-substituent embedded in the styrene. The resulting isoindolinones are valuable building blocks for the synthesis of bioactive compounds. They provide easy access to the natural-product-like compounds, isoindolobenzazepines, in a one-pot two-step reaction. Selected isoindolinones inhibited Hedgehog (Hh)-dependent differentiation of multipotent murine mesenchymal progenitor stem cells into osteoblasts.
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