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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

208 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)13451-13457
Number of pages7
JournalAngewandte Chemie - International Edition
Volume59
Issue number32
DOIs
Publication statusPublished - 3 Aug 2020
Externally publishedYes

Keywords

  • asymmetric C−H activation
  • biaryls
  • helicene
  • palladium
  • transient directing group

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