Site-Selective C(sp3)–H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst

Takahide Fukuyama, Tomohiro Nishikawa, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

The TBADT-catalyzed C(sp3)–H functionalization of perfluorophenyl- and perfluoroalkyl-substituted alkanes was studied to determine how the fluorous substituents affect site-selectivity. Alkylation of alkyl-substituted perfluorobenzene avoids α-C–H bonds, unlike their alkylbenzene counterparts, allowing site-selective functionalization of C–H bonds remote to the aromatic ring. Alkylation of alkanes having a perfluoroalkyl group also avoided α-C–H bonds. Radical polar effects in the SH2 transition states could explain this avoidance of α-C–H functionalization.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
StateAccepted/In press - 1 Jan 2019

Keywords

  • C–H functionalization
  • Photocatalysis
  • Radical reactions
  • Synthetic methods

Fingerprint Dive into the research topics of 'Site-Selective C(sp<sup>3</sup>)–H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst'. Together they form a unique fingerprint.

  • Cite this