Experimental and Computational Study on the Anti-Markovnikov Hydrofunctionalization of Olefins Using Glycine-Extended AQ-Auxiliaries

Fred U. Nnamdi, Colin Diner, Pier Alexandre Champagne, Michael G. Organ

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Two similar tridentate directing groups derived from glycine and 8-aminoquinoline were shown to enable the palladium-catalyzed anti-Markovnikov hydrofunctionalization of 4-pentenylamine with drastically different efficiencies. A computational investigation into the origin of the reactivity difference between these isomeric, carbonyl-transposed auxiliaries suggests that protonation state, thus charge of the substrate-metal complex prior to nucleopalladation is key. These investigations have culminated in a directing group design that can undergo Pd-catalyzed hydrofunctionalization under relatively mild conditions, as low as room temperature.

Original languageEnglish (US)
Pages (from-to)3855-3860
Number of pages6
JournalChemistry - A European Journal
Volume27
Issue number11
DOIs
StatePublished - Feb 19 2021

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • catalysis
  • computations
  • directing group
  • mechanistic study
  • palladium

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