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Design and Development of Quinone Ca...

The University of Wisconsin - Madison.

Design and Development of Quinone Catalysts for Aerobic C--N Bond Dehydrogenation Reactions.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Design and Development of Quinone Catalysts for Aerobic C--N Bond Dehydrogenation Reactions.
Author:	Wendlandt, Alison E.
Description:	432 p.
Notes:	Source: Dissertation Abstracts International, Volume: 76-11(E), Section: B.
Notes:	Adviser: Shannon S. Stahl.
Contained By:	Dissertation Abstracts International76-11B(E).
Subject:	Organic chemistry.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3708000
ISBN:	9781321829006

Design and Development of Quinone Catalysts for Aerobic C--N Bond Dehydrogenation Reactions.
Wendlandt, Alison E.

Design and Development of Quinone Catalysts for Aerobic C--N Bond Dehydrogenation Reactions. - 432 p.

Source: Dissertation Abstracts International, Volume: 76-11(E), Section: B.

Thesis (Ph.D.)--The University of Wisconsin - Madison, 2015.

The selective oxidation of organic compounds is a prominent challenge in organic chemistry. Towards this goal, molecular oxygen is an ideal oxidant. Uncatalyzed aerobic oxidation reactions have found important application in the commodity scale synthesis of certain compounds. However, such autoxidation reactions are intrinsically substrate-controlled. More frequently, selective aerobic oxidations are achieved by using a catalyst to promote the desired transformation. Under such a regime the identity of the catalyst -- and therefore the reaction mechanism -- dictates the chemical outcome of the reaction. The development of new catalysts which promote aerobic oxidation reactions is therefore of great significance.

ISBN: 9781321829006Subjects--Topical Terms:

708640
Organic chemistry.

Design and Development of Quinone Catalysts for Aerobic C--N Bond Dehydrogenation Reactions.
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245 1 0 $a Design and Development of Quinone Catalysts for Aerobic C--N Bond Dehydrogenation Reactions.
300 $a 432 p.
500 $a Source: Dissertation Abstracts International, Volume: 76-11(E), Section: B.
500 $a Adviser: Shannon S. Stahl.
502 $a Thesis (Ph.D.)--The University of Wisconsin - Madison, 2015.
520 $a The selective oxidation of organic compounds is a prominent challenge in organic chemistry. Towards this goal, molecular oxygen is an ideal oxidant. Uncatalyzed aerobic oxidation reactions have found important application in the commodity scale synthesis of certain compounds. However, such autoxidation reactions are intrinsically substrate-controlled. More frequently, selective aerobic oxidations are achieved by using a catalyst to promote the desired transformation. Under such a regime the identity of the catalyst -- and therefore the reaction mechanism -- dictates the chemical outcome of the reaction. The development of new catalysts which promote aerobic oxidation reactions is therefore of great significance.
520 $a This thesis highlights two classes of catalyst that promote selective aerobic oxidation reactions. Chapters 1-4 describe the development of a family of o-quinone catalysts based on o-quinone cofactors found in certain oxidase and dehydrogenase enzymes. Unlike the natural cofactors, which have limited substrate scope, we find evidence for an unnatural reaction pathway that broadens the synthetic utility of these reagents. This family of bioinspired o-quinone catalysts is particularly effective in the aerobic dehydrogenation of C---N bonds. Subsequently, in chapters 5 and 6 I discuss the application of Cu-based catalysts to aerobic oxidation reactions, emphasizing an apparent mechanistic bifurcation between single electron transfer-based mechanisms and organometallic mechanisms within the published literature. Further work describes an application of CuII reagents in the aerobic oxidative cyclization of enamides to oxazoles.
590 $a School code: 0262.
650 4 $a Organic chemistry. $3 708640
650 4 $a Inorganic chemistry. $3 708705
650 4 $a Analytical chemistry. $3 708695
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710 2 $a The University of Wisconsin - Madison. $b Chemistry. $3 730297
773 0 $t Dissertation Abstracts International $g 76-11B(E).
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