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Rh III ‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones
Author(s) -
Shaaban Saad,
Davies Caitlin,
Merten Christian,
Flegel Jana,
Otte Felix,
Strohmann Carsten,
Waldmann Herbert
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002384
Subject(s) - chemistry , catalysis , regioselectivity , aryl , substituent , styrene , combinatorial chemistry , surface modification , medicinal chemistry , organic chemistry , alkyl , polymer , copolymer
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.