Rhodium(III) Catalyst for Regioselective Activation of C–H Bonds

  • ChemPubSoc Europe Logo
  • Author: Chemistry – A European Journal
  • Published Date: 21 November 2018
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Rhodium(III) Catalyst for Regioselective Activation of C–H Bonds

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The rhodium(III)-catalyzed C–H activation of aromatic compounds allows the synthesis of complex heterocyclic molecules from simple starting materials in a single step. This method is particularly useful for the directed search for drug candidates and other biologically active molecules. However, controlling the chemo- and regioselectivity of the C–H-activation reactions is often challenging.

Dmitry Perekalin, Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, and colleagues have developed a rhodium(III)-based catalyst for C–H activation. The catalyst, [(C5H2tBu2CH2tBu)RhCl2]2, converts activated aromatic amides and alkenes into biologically active 4‐substituted dihydroisoquinolones (pictured). The desired products were obtained in yields of 72–97 %.

The cyclopentadienyl ligand of the catalyst complex was constructed via an unusual cyclization of three molecules of tert-butylacetylene. The bulky tert-butyl groups provide a high regioselectivity by blocking undesired reaction pathways. The designed catalyst could also help to improve regioselectivity of other C–H activation reactions.



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