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Rh^III -Catalyzed C-H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones.

ABSTRACT: Rh^III -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.

SUBMITTER: Shaaban S

PROVIDER: S-EPMC7496876 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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RhIII -Catalyzed C-H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones.

Shaaban Saad S Shaaban Saad S Davies Caitlin C Merten Christian C Flegel Jana J Otte Felix F Strohmann Carsten C Waldmann Herbert H

Chemistry (Weinheim an der Bergstrasse, Germany) 20200721 47

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 ...[more]

PMID: 32428319

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