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Regiodivergent C−H and Decarboxylative C−C Alkylation by Ruthenium Catalysis: ortho versus meta Position‐Selectivity

Korvorapun, Korkit ; Moselage, Marc ; Struwe, Julia ; Rogge, Torben ; Messinis, Antonis M. ; Ackermann, Lutz

Angewandte Chemie (International ed.), 2020-10, Vol.59 (42), p.18795-18803 [Periódico revisado por pares]

Germany: Wiley Subscription Services, Inc

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  • Título:
    Regiodivergent C−H and Decarboxylative C−C Alkylation by Ruthenium Catalysis: ortho versus meta Position‐Selectivity
  • Autor: Korvorapun, Korkit ; Moselage, Marc ; Struwe, Julia ; Rogge, Torben ; Messinis, Antonis M. ; Ackermann, Lutz
  • Assuntos: Alkylation ; Catalysis ; C−C activation ; C−H activation ; decarboxylation ; Ruthenium ; Selectivity
  • É parte de: Angewandte Chemie (International ed.), 2020-10, Vol.59 (42), p.18795-18803
  • Notas: These authors contributed equally to this work.
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  • Descrição: Ruthenium(II)biscarboxylate complexes enabled the selective alkylation of C−H and C−C bonds at the ortho‐ or meta‐position. ortho‐C−H Alkylations were achieved with 4‐, 5‐ as well as 6‐membered halocycloalkanes. Furthermore, the judicious choice of the directing group allowed for a full control of ortho‐/meta‐selectivities. Detailed mechanistic studies by experiment and computation were performed and provided strong support for an oxidative addition/reductive elimination process for ortho‐alkylations, while a homolytic C−X cleavage was operative for the meta‐selective transformations. Ortho vs. meta: C−H alkylations of arylpyrazoles are achieved through ruthenium‐catalyzed C−H or C−C activation. The site‐selectivity is controlled by the pyrazole substituents and the steric hindrance of the alkyl moiety.
  • Editor: Germany: Wiley Subscription Services, Inc
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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