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A Vinyl-Cation-Induced 1,3-Aryl Shift.

Liang Fu1, Helena Damsen1, Meike Niggemann1

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 4, 2017
PubMed
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This study introduces a novel method for carbon-carbon bond formation using benzylic alcohols and alkynes. The reaction, driven by cation rearrangement, efficiently produces valuable heterocyclic compounds.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Formation of C-C bonds is crucial in organic synthesis.
  • Benzylic alcohols are versatile starting materials.
  • Alkynes are important building blocks.

Purpose of the Study:

  • To develop a new method for C-C bond insertion into benzylic alcohols.
  • To utilize a vinyl cation to allyl cation rearrangement for a 1,3-carbon shift.
  • To synthesize heterocyclic compounds like dihydroquinolines and chromenes.

Main Methods:

  • Reaction of benzylic alcohols with internal alkynes.
  • Catalysis using aluminum triflate (Al(OTf)3).
  • Employing vinyl cation to allyl cation rearrangement mechanism.
Keywords:
aluminum catalysiscarbon shiftcation rearrangementtransition-metal freevinyl cation

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Main Results:

  • Achieved net insertion of alkyne into sp2-sp3 C-C bond.
  • High selectivity for the 1,3-carbon shift rearrangement.
  • Successful synthesis of various 1,2-dihydroquinolines and 2H-chromenes.

Conclusions:

  • Developed an efficient and selective method for C-C bond formation.
  • Demonstrated the utility of aluminum triflate as a catalyst.
  • Provided access to valuable heterocyclic scaffolds.