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Catalytic transfer zincation using ammonium cations.

Justyna Łosiewicz1, Milan Kumar Bisai1, Gary S Nichol1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, UK. mingleso@ed.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|August 22, 2025
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Summary
This summary is machine-generated.

This study introduces a new catalytic method for heteroaryl C-H zincation, controlled electronically rather than by substrate acidity. The findings highlight the impact of anion choice and steric effects on reaction efficiency.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Traditional C-H zincation relies on substrate pKa for selectivity.
  • Developing new catalytic methods for organozinc compound synthesis is crucial.

Purpose of the Study:

  • To develop a novel, electronically controlled catalytic heteroaryl C-H zincation method.
  • To investigate the role of anions and steric effects in transfer zincation.

Main Methods:

  • Utilized a (β-diketiminate)Zn-Me complex and [(R3N)H][Anion] salt.
  • Explored different counteranions, including [B(C6F5)4]- and [CHB11H5Br6]-.
  • Investigated catalytic C-H borylation using the same reagents.

Main Results:

  • Achieved electronically controlled heteroaryl C-H zincation.
  • Demonstrated anion dependence, with [B(C6F5)4]- being superior.
  • Identified steric hindrance in zinc-ethyl systems as a factor increasing protonolysis barrier.

Conclusions:

  • Catalytic electrophilic transfer zincation is feasible.
  • Anion coordination and steric factors significantly influence reaction pathways and efficiency.
  • The study provides insights into transition state sensitivity in organometallic reactions.