Cooperative Polar/Steric Strategy in Achieving Site-Selective Photocatalyzed C(sp3)−H Functionalization

Keiichi Yamada, Takahide Fukuyama, Saki Fujii, Davide Ravelli, Maurizio Fagnoni, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Synergistic control over the SH2 transition states of hydrogen abstraction exploiting polar and steric effects provides a promising cooperative strategy for site-selective C(sp3)−H functionalization using decatungstate anion photocatalysis. By using this photocatalytic approach, the C−H bonds of substituted lactones and cyclic ketones were functionalized selectively. In the remarkable case of 2-isoamyl 4-tert-butyl cyclohexanone (1 t) bearing five methyl, five methylene, and three methine C−H bonds, one methine C−H bond in the isoamyl tether was selectively functionalized.

Original languageEnglish
Pages (from-to)8615-8618
Number of pages4
JournalChemistry - A European Journal
Volume23
Issue number36
DOIs
StatePublished - 27 Jun 2017

Keywords

  • C−H functionalization
  • decatungstate
  • photocatalysis
  • site-selectivity
  • steric effects

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