Cyclic Peroxide Oxidation of Aromatic Compounds

Physical Sciences : Chemical

Available for licensing

Inventors

  • Dionicio Siegel , Chemistry and Biochemistry
  • Changxia Yuan , University of Texas at Austin
  • Andrew Camelio , University of Texas at Austin
  • Anders Eliasen , University of Texas at Austin
  • Trevor Johnson , University of Texas at Austin
  • Abram Axelrod , University of Texas at Austin

Background/unmet need

Methods for C-H bond oxidation play a fundamental role in process chemistry, providing functionality that is required in the final target or that enables subsequent transformations.

The oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, was previously a challenge with the direct hydroxylation of arenes achieved through the use of strong Brønsted or Lewis acid to mediated electrophilic aromatic substitution reactions with super-stoichiometric equivalents of oxidants, significantly limiting the scope of the reaction. As the products of these reactions are more reactive than the starting materials, overoxidation is frequently a competitive process. Transition-metal catalysed C-H oxidation of arenes with or without directing groups has been developed, improving upon the acid-mediated process; however, precious metals are required.

Herein the inventors demonstrate that a simple peroxide reagent alone functions as a selective oxidant for the transformation of arenes to phenols under mild conditions.

Invention Description

The inventors have developed a novel and cost-effective method for the oxidation of aromatic compounds to the corresponding phenols. The reagent for the chemical transformation is readily prepared from commodity chemicals and can be recovered and recycled from the reaction.

Although the reaction proceeds through a radical mechanism, aromatic C-H bonds are selectively oxidized in preference to activated Csp3-H bonds. Importantly, a wide array of functional groups are compatible with this reaction.

Benefits/Advantages

  • Low cost
  • No over-oxidation
  • Predictable regioselectivity

Features

  • Functional group compatibility
  • Predictable regioselectivity
  • Low cost
  • No over-oxidation

Market potential/applications

Research laboratories, chemical manufactures, pharmaceutical companies

Development Stage

Lab/bench prototype