IP Library Granted Patent US 9,469,602
Granted Patent B2
US 9,469,602 · App. 14/530,150 · Granted Oct 18, 2016

Redox-auxiliary catalysis

Inventors: Silas Blackstock (Tuscaloosa, AL); Lester Gray (Tuscaloosa, AL); Melody Kelley (Tuscaloosa, AL); Carl Saint-Louis (Tuscaloosa, AL)
Assignee: The Board of Trustees of the University of Alabama
C07C245/08C07C309/73C07F17/02H01L31/00C07C2102/42
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Quick Facts
Patent No.
US 9,469,602
App. No.
14/530,150
Granted
Oct 18, 2016
Kind
B2
Abstract

Disclosed herein is a method of activating a compound for a chemical reaction comprising functionalizing a compound with a redox auxiliary group and oxidizing the redox auxiliary group that is bonded to the compound, thereby activating the compound, wherein the activated compound undergoes a chemical reaction to form a product and the oxidation of the redox auxiliary group is reversible. Methods of making and using these materials are also disclosed.

Claims (16)

1. A compound defined by Formula V:

wherein X 1 -X 5 are independently chosen from hydrogen, halogen, C 1 -C 24 alkyl, C 2 -C 24 alkenyl, C 2 -C 24 alkynyl, aryl, heteroaryl, alkoxyl, hydroxy, nitrile, nitro, —C(O)R 1 , —NR 1 R 2 , —C(O)NR 1 R 2 ;

wherein R 1 and R 2 are independently chosen from hydrogen, halogen, C 1 -C 24 alkyl, C 2 -C 24 alkenyl, C 2 -C 24 alkynyl, C 1 -C 24 aryl and C 1 -C 24 heteroaryl, and

wherein Mc is a metallocene.

2. The compound of claim 1 , wherein the compound is defined by Formula VI:

wherein Ts is a tosyl group, and

wherein Fc is a ferrocene.

3. A method of activating a compound for a chemical reaction, comprising:

a) providing the compound of claim 1 ; and

b) oxidizing the redox auxiliary group that is bonded to the compound, thereby activating the compound of claim 1 ;

wherein the activated compound undergoes a chemical reaction to form a product, and

wherein the oxidation of the redox auxiliary group is reversible.

4. The method of claim 3 , wherein the redox auxiliary group is oxidized photochemically, electrochemically, or a combination thereof.

5. The method of claim 3 , wherein the oxidized redox auxiliary group exchanges an electron with a neutral redox auxiliary group to propagate electron transfer chain reaction to effect redox catalysis.

6. The method of claim 3 , further comprising the step of removing the redox auxiliary group from the product.

7. The method of claim 3 , wherein the reaction is an isomerization, a rearrangement, an electrocyclic reaction, a photoelectrochemical reaction, a thermal reaction, or a combination thereof.

Assignments (2)
CONFIRMATORY LICENSE Recorded Apr 8, 2015
From: UNIVERSITY OF ALABAMA
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 035387/0022 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2014
From: BLACKSTOCK, SILAS; GRAY, LESTER; KELLEY, MELODY; SAINT-LOUIS, CARL
To: THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ALABAMA
Reel/Frame 034118/0709 →
Continuity (2)
Provisional Application 61898716 · Nov 1, 2013
Related Publication 20150133646A1 · May 14, 2015