Small Aromatic Molecule Synthesis at Ambient Conditions Using Diels-Alder Reactions and Benzyne Intermediates

Technology No. 20120115
IP Status: Issued US Patent; Application #: 13/756,069

Small Molecule Synthesis at Ambient Conditions

A method has been developed to synthesize small molecules with complex aromatic core structures in high yields and at ambient conditions without a catalyst. By reducing the number of steps in the synthesis, the method has the potential to reduce the cost and increase efficiency in the synthesis of drugs, dyes and other aromatic compounds.

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High-Yield Diels-Alder Synthesis of Benzyne Intermediates

The method involves utilizing a Diels-Alder reaction to produce benzyne as part of the molecule, an intermediate which rearranges to give the target molecule. The reaction is thermodynamically favorable, so proceeds at room temperature without the need for a catalyst or other harsh conditions. This is in contrast to the conventional method of producing aromatic compounds, which generally require use of a strong base.


BENEFITS OF SMALL MOLECULE SYNTHESIS USING BENZYNE INTERMEDIATES:

  • The method is versatile with over 30 products synthesized so far.
  • The method proceeds under ambient conditions without catalyst.
  • The majority of yields produced by this method are in excess of 75%.


Researchers
Thomas R. Hoye, PhD
Distinguished Teaching Professor, Chemistry
External Link (www.chem.umn.edu)

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