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Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes

Dhawa, Uttam ; Tian, Cong ; Wdowik, Tomasz ; Oliveira, João C. A. ; Hao, Jiping ; Ackermann, Lutz

Angewandte Chemie (International ed.), 2020-08, Vol.59 (32), p.13451-13457 [Periódico revisado por pares]

Weinheim: Wiley Subscription Services, Inc

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  • Título:
    Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes
  • Autor: Dhawa, Uttam ; Tian, Cong ; Wdowik, Tomasz ; Oliveira, João C. A. ; Hao, Jiping ; Ackermann, Lutz
  • Assuntos: asymmetric C−H activation ; Asymmetry ; biaryls ; Catalysis ; Catalysts ; Dicarboxylic acids ; Electrochemistry ; Enantiomers ; helicene ; Mode of action ; palladium ; transient directing group
  • É parte de: Angewandte Chemie (International ed.), 2020-08, Vol.59 (32), p.13451-13457
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Asymmetric pallada‐electrocatalyzed C−H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective C−H activations were realized with high position‐, diastereo‐, and enantio‐control under mild reaction conditions to obtain highly enantiomerically‐enriched biaryls and fluorinated N−C axially chiral scaffolds. Our strategy provided expedient access to, among others, novel chiral BINOLs, dicarboxylic acids and helicenes of value to asymmetric catalysis. Mechanistic studies by experiments and computation provided key insights into the catalyst's mode of action. EE: Enantioselective Electrocatalysis was realized in terms of asymmetric C−H activation through transient directing group (TDG)‐enabled pallada‐electrocatalysis. Experiments and calculations rationalize the key transition states, while asymmetric electrocatalysis provided step‐economical access to axially chiral bi(hetero)aryl diols, diacids and helicenes.
  • Editor: Weinheim: Wiley Subscription Services, Inc
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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