Site-Selective C-H Functionalization by Decatungstate Anion Photocatalysis: Synergistic Control by Polar and Steric Effects Expands the Reaction Scope

Davide Ravelli, Maurizio Fagnoni*, Takahide Fukuyama, Tomohiro Nishikawa, Ilhyong Ryu

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

97 Scopus citations

Abstract

The synergistic control of the SH2 transition states of hydrogen abstraction by polar and steric effects provides a promising strategy in achieving site-selective C(sp3)-H functionalization under decatungstate anion photocatalysis. By using this photocatalytic approach, the C-H bonds of alkanes, alcohols, ethers, ketones, amides, esters, nitriles, and pyridylalkanes were functionalized site-selectively. In the remarkable case of a 2,4-disubstituted cyclohexanone 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)701-713
Number of pages13
JournalACS Catalysis
Volume8
Issue number1
DOIs
StatePublished - 5 Dec 2017

Keywords

  • C(sp3)−H functionalization
  • alkanes
  • carbonyl compounds
  • decatungstate anion
  • nitriles
  • photocatalysis
  • polar effects
  • steric effects

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