Asymmetric Photocatalytic C-H Functionalization of Toluene and Derivatives.

Reported herein is a visible-light-mediated organocatalytic direct C-H functionalization of toluene derivatives to afford enantioenriched β-benzylated aldehydes from the corresponding enals. The process combines the oxidative power of a chiral excited-state iminium ion and the basic nature of its counteranion to trigger the generation of benzylic radicals by means of a sequential multisite proton-coupled electron transfer mechanism. This study shows that feedstock chemicals generally used as solvents, such as toluene and xylene derivatives, can be used as substrates for making chiral molecules with high enantioselectivity.

• Publication year

  2018

• Venue

  Journal of the American Chemical Society

• Publication date

  2018-06-22

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/jacs.8b05240PMID 29932655
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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