Metal-free oxidation of pyrenes
AssigneeArizona Board of Regents on Behalf of the University of Arizona
InventorsDominic V. McGrath, Tarek H. El Assaad
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Abstract
The present invention provides a method for oxidizing pyrenes without any metal-mediated catalyst or reagent. In particular, the present invention provides a method for selectively oxidizing the K-region of pyrenes using a meta-free oxidizing agent to produce a pyrene 4,5-dione and/or a pyrene 4,5,9,10-tetraone compounds.
Claims24
A process for oxidizing a pyrene compound according to Formula I:
- the process comprising contacting the pyrene compound according to Formula I with a metal-free oxidizing agent under conditions sufficient to produce a pyrene 4,5-dione according to Formula II or a pyrene 4,5,9,10-tetraone compound according to Formula III:
- wherein
- each of R1 and R2 are independently an alkyl, an aryl, or a heteroaryl, and
- the metal-free oxidizing agent comprises a hypervalent iodine oxyacid, a hypervalent iodine, or any mixture thereof.
A method for producing a pyrene 4,5-dione compound according to Formula II from a pyrene compound according to Formula I, the method comprising:
- contacting the pyrene compound according to Formula I;
- with less than 6 molar equivalents of a metal-free oxidizing agent under conditions sufficient to produce the pyrene 4,5-dione compound according to Formula II:
- wherein each of R1 and R2 are independently alkyl, aryl, or heteroaryl,
- wherein the metal-free oxidizing agent comprises a hypervalent iodine oxyacid, a hypervalent iodine, or any mixture thereof.
A method for producing a pyrene 4,5,9,10-tetraone compound according to Formula III from a pyrene compound according to Formula I, the method comprising:
- contacting the pyrene compound according to Formula I:
- with greater than 6 molar equivalents of a metal-free oxidizing agent under conditions sufficient to produce the pyrene 4,5,9,10-tetraone compound according to Formula III:
- wherein each of R1 and R2 are independently alkyl, aryl, or heteroaryl, and
- wherein the metal-free oxidizing agent comprises a hypervalent iodine oxyacid, a hypervalent iodine, or any mixture thereof.
Dependencies are inferred from the claim text.