Site-selectivity in TBADT-photocatalyzed C(sp3)H functionalization of saturated alcohols and alkanes

Takahide Fukuyama, Keiichi Yamada, Tomohiro Nishikawa, Davide Ravelli, Maurizio Fagnoni, Ilhyong Ryu

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Site-selectivity in C(sp3)H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, CH bond a to the hydroxy group was preferentially functionalized. The a-site-selectivity is rationalized by polar effects imparted by the hydroxy group in the SH2 transition states. In contrast, CH functionalization of alkanes was largely affected by steric effects.

Original languageEnglish
Pages (from-to)207-209
Number of pages3
JournalChemistry Letters
Volume47
Issue number2
DOIs
StatePublished - 1 Jan 2018

Keywords

  • C-H functionalization
  • Decatungstate anion
  • Photocatalysis

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