Direct catalytic trifluoromethylthiolation of boronic acids and alkynes employing electrophilic shelf-stable N-(trifluoromethylthio)phthalimide

Roman Pluta, Pavlo Nikolaienko, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

193 Scopus citations

Abstract

A new and safe method for the synthesis of N-(trifluoromethylthio) phthalimide, a convenient and shelf-stable reagent for the direct trifluoromethylthiolation, has been developed. N-(Trifluoromethylthio) phthalimide can be used as an electrophilic source of F3CS + and reacts readily with boronic acids and alkynes under copper catalysis. The utility of CF3S-containing molecules as biologically active agents, the mild reaction conditions employed, and the high tolerance of functional groups demonstrate the potential of this new methodology to be widely applied in organic synthesis as well as industrial pharmaceutical and agrochemical research and development. Shelf life: A new and safe method for the synthesis of N-(trifluoromethylthio)phthalimide has been developed. It serves as a convenient and shelf-stable reagent for the direct copper-catalyzed trifluoromethylthiolation of readily available boronic acids and alkynes.

Original languageEnglish (US)
Pages (from-to)1650-1653
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number6
DOIs
StatePublished - Feb 3 2014
Externally publishedYes

Keywords

  • alkynes
  • boron
  • copper
  • homogeneous catalysis
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Direct catalytic trifluoromethylthiolation of boronic acids and alkynes employing electrophilic shelf-stable N-(trifluoromethylthio)phthalimide'. Together they form a unique fingerprint.

Cite this