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Related Experiment Videos

Reversible Oxidative Addition at Carbon.

Antonius F Eichhorn1, Sonja Fuchs1, Marco Flock1

  • 1Institut für Anorganische Chemie and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.

Angewandte Chemie (International Ed. in English)
|April 8, 2017
PubMed
Summary
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N-heterocyclic carbenes (NHCs) and cyclic alkyl amino carbenes (cAACs) form reversible adducts with arylboronate esters. Cyclic alkyl amino carbenes also undergo oxidative addition, leading to ring-expanded products.

Area of Science:

  • Organometallic Chemistry
  • Carbene Chemistry
  • Boron Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) and cyclic alkyl amino carbenes (cAACs) are important classes of ligands in organometallic chemistry.
  • Arylboronate esters are versatile building blocks in organic synthesis.

Purpose of the Study:

  • To investigate the reactivity of NHCs and cAACs with arylboronate esters.
  • To characterize the resulting adducts and reaction products.

Main Methods:

  • Reaction of NHCs and cAACs with various arylboronate esters.
  • Spectroscopic characterization (NMR) of reaction products.

Main Results:

  • NHCs form reversible Lewis acid/base adducts with arylboronate esters.
Keywords:
B−C bond activationN-heterocyclic carbenesarylboronate esterscyclic alkyl amino carbenes

Related Experiment Videos

  • cAACs form adducts with catecholboronate esters, which can further react to form ring-expanded products.
  • cAACs react with other boronate esters via reversible B-C oxidative addition to form new carbene-boron species.

    • Conclusions:

    • The reactivity of NHCs and cAACs with arylboronate esters is diverse, leading to adduct formation and oxidative addition pathways.
    • The observed reactions highlight the tunable electronic and steric properties of these carbenes in interactions with boron compounds.