4.8 Article

Atropoenantioselective palladaelectro-catalyzed anilide C-H olefinations viable with natural sunlight as sustainable power source

Journal

CHEMICAL SCIENCE
Volume 13, Issue 9, Pages 2729-2734

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc06135f

Keywords

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Funding

  1. ERC [101021358]
  2. DFG (Gottfried-Wilhelm-Leibniz award)
  3. CSC
  4. European Research Council (ERC) [101021358] Funding Source: European Research Council (ERC)

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In this study, chiral-selective para-electrocatalytic reactions were achieved for C-H olefination and C-H allylation under extremely mild conditions. The method does not require the use of environmentally harmful silver salts and the resource-economy of the transformation was further improved by directly employing renewable solar energy.
Enantioselective electrocatalyzed transformations represent a major challenge. We herein achieved atropoenantioselective pallada-electrocatalyzed C-H olefinations and C-H allylations with high efficacy and enantioselectivity under exceedingly mild reaction conditions. With (S)-5-oxoproline as the chiral ligand, activated and non-activated olefins were suitable substrates for the electro-C-H activations. Dual catalysis was devised in terms of electro-C-H olefination, along with catalytic hydrogenation. Challenging enantiomerically-enriched chiral anilide scaffolds were thereby obtained with high levels of enantio-control in the absence of toxic and cost-intensive silver salts. The resource-economy of the transformation was even improved by directly employing renewable solar energy.

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