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From Palladium to Nickel : = The Carboiodination Reaction Forward and Back.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	From Palladium to Nickel :/
其他題名:	The Carboiodination Reaction Forward and Back.
作者:	Marchese, Austin D.
面頁冊數:	1 online resource (888 pages)
附註:	Source: Dissertations Abstracts International, Volume: 84-06, Section: B.
Contained By:	Dissertations Abstracts International84-06B.
標題:	Organic chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=29395030click for full text (PQDT)
ISBN:	9798357551894

From Palladium to Nickel : = The Carboiodination Reaction Forward and Back.
Marchese, Austin D.

From Palladium to Nickel :The Carboiodination Reaction Forward and Back. - 1 online resource (888 pages)

Source: Dissertations Abstracts International, Volume: 84-06, Section: B.

Thesis (Ph.D.)--University of Toronto (Canada), 2022.

Includes bibliographical references

For the past half-century, transition-metal catalysis has been an essential part of developing economical, sustainable and efficient strategies to generate pharmaceutically relevant small molecules. Despite the tremendous progress made towards these goals, new synthetic approaches are needed to keep up with the demand for innovation in drug production and discovery. Our group has had a mission to discover atom-economical processes that enable rapid access to a wide array of halogenated heterocycles. We have popularized a strategy known as the carbohalogenation reaction, wherein an aryl/acyl group and a halogen are transferred across a tethered π-bond, generating a cyclic product. Early success was achieved using palladium catalysis, however many limitations remained. First, can we access previously unattainable stereoisomers, whether it be enantioenriched products or different diastereomers? How can we reach a more structurally broad class of halogenated molecules? Lastly, what is the reaction mechanism using different catalysts?Motivated by a shift in the field to convert from precious metals to earth abundant base metals, in 2017 we began our exploration with nickel to answer these questions. Chapter 1 contains necessary background information on transition-metal catalyzed halogenation methods, domino Mizoroki-Heck reactions and landmark reports of carboiodination reactions. Chapter 2 describes the development of the first nickel-catalyzed carboiodination reaction. The following four chapters outline unique reports of nickel-carboiodination reactions, each focusing on fundamental limitations in the field, culminating with the first enantioselective nickel-catalyzed carboiodination reaction in chapter 6.Chapters 7 and 8 focus on the use of palladium in domino reactions. Chapter 7 contains the synthesis of medicinally relevant bis-heterocyclic spirocycles, via a palladium catalyzed domino Mizoroki-Heck/C-H activation reaction. Employing the knowledge of the previous work, chapter 8 combines nickel carboiodination chemistry and palladium C-H activation reactions. Fundamentally, all reactions are microscopically reversible, though studying the reversibility of Mizoroki-Heck reactions is challenging. Enabled by compounds obtained via our carboiodination methodologies, this chapter outlines our comprehensive study of the reversible C-C bond formation using palladium catalysis. Herein, we focus on mechanistic elucidation, development of a diastereoconvergent methodology, as well as study electronic and steric parameters effecting the reaction.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2023

Mode of access: World Wide Web

ISBN: 9798357551894Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

CatalysisIndex Terms--Genre/Form:

542853
Electronic books.

From Palladium to Nickel : = The Carboiodination Reaction Forward and Back.
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500 $a Source: Dissertations Abstracts International, Volume: 84-06, Section: B.
500 $a Advisor: Lautens, Mark.
502 $a Thesis (Ph.D.)--University of Toronto (Canada), 2022.
504 $a Includes bibliographical references
520 $a For the past half-century, transition-metal catalysis has been an essential part of developing economical, sustainable and efficient strategies to generate pharmaceutically relevant small molecules. Despite the tremendous progress made towards these goals, new synthetic approaches are needed to keep up with the demand for innovation in drug production and discovery. Our group has had a mission to discover atom-economical processes that enable rapid access to a wide array of halogenated heterocycles. We have popularized a strategy known as the carbohalogenation reaction, wherein an aryl/acyl group and a halogen are transferred across a tethered π-bond, generating a cyclic product. Early success was achieved using palladium catalysis, however many limitations remained. First, can we access previously unattainable stereoisomers, whether it be enantioenriched products or different diastereomers? How can we reach a more structurally broad class of halogenated molecules? Lastly, what is the reaction mechanism using different catalysts?Motivated by a shift in the field to convert from precious metals to earth abundant base metals, in 2017 we began our exploration with nickel to answer these questions. Chapter 1 contains necessary background information on transition-metal catalyzed halogenation methods, domino Mizoroki-Heck reactions and landmark reports of carboiodination reactions. Chapter 2 describes the development of the first nickel-catalyzed carboiodination reaction. The following four chapters outline unique reports of nickel-carboiodination reactions, each focusing on fundamental limitations in the field, culminating with the first enantioselective nickel-catalyzed carboiodination reaction in chapter 6.Chapters 7 and 8 focus on the use of palladium in domino reactions. Chapter 7 contains the synthesis of medicinally relevant bis-heterocyclic spirocycles, via a palladium catalyzed domino Mizoroki-Heck/C-H activation reaction. Employing the knowledge of the previous work, chapter 8 combines nickel carboiodination chemistry and palladium C-H activation reactions. Fundamentally, all reactions are microscopically reversible, though studying the reversibility of Mizoroki-Heck reactions is challenging. Enabled by compounds obtained via our carboiodination methodologies, this chapter outlines our comprehensive study of the reversible C-C bond formation using palladium catalysis. Herein, we focus on mechanistic elucidation, development of a diastereoconvergent methodology, as well as study electronic and steric parameters effecting the reaction.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2023
538 $a Mode of access: World Wide Web
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653 $a Catalysis
653 $a Heterocycles
653 $a Nickel
653 $a Palladium
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690 $a 0490
710 2 $a ProQuest Information and Learning Co. $3 783688
710 2 $a University of Toronto (Canada). $b Chemistry. $3 3178441
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