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Radical Cross-Coupling Enabled by Functionalized Electrodes.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Radical Cross-Coupling Enabled by Functionalized Electrodes./
Author:	Palkowitz, Maximilian D.
Description:	1 online resource (937 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 84-07, Section: B.
Contained By:	Dissertations Abstracts International84-07B.
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=29328347click for full text (PQDT)
ISBN:	9798368412306

Radical Cross-Coupling Enabled by Functionalized Electrodes.
Palkowitz, Maximilian D.

Radical Cross-Coupling Enabled by Functionalized Electrodes. - 1 online resource (937 pages)

Source: Dissertations Abstracts International, Volume: 84-07, Section: B.

Thesis (Ph.D.)--The Scripps Research Institute, 2023.

Includes bibliographical references

The development of new electrochemical transformations has had a profound impact on the state of organic synthesis. While the use of electrochemistry in organic synthesis dates back several decades, recent efforts to lower the barrier to entry to this technology has allowed to community to embrace this technology more rapidly. These include the development of standardized commercial reactors and a wellspring of educational resources tailored toward synthetic chemists. To this end, our laboratory has sought electrochemical solutions to challenging synthetic problems. Electrochemistry gives the practitioner several unique advantages such as chemoselectivity through control of potential/current, safety by mimicry of harsh chemical reagents, and ease of scalability. Combination of these principles as well as many others that have not been mentioned has brought forth the development of enabling methodology for complex molecule synthesis in the modern age. This doctoral. thesis covers the development of practical C(sp2)-C(sp3) cross-coupling tactics that hinge upon electrode functionalization with silver nanoparticles (Ag-NP). These functionalized electrodes support otherwise challenging Ni-catalytic cross--coupling reactions between activated alkyl carboxylic acids in the form of redox active esters and C(sp2) alkenyl and heteroaryl electrophiles. Chapter 1 provides relevant background on the fundamentals of synthetic organic electrochemistry. Chapter 2 involves the discovery and mechanistic underpinnings of these Ag-NP functionalized electrodes and how their implementation in electrochemical decarboxylative alkenylation can enable a modular platform for terpene synthesis. Chapter 3 takes the key reactivity and mechanistic understandings discovered in the context of an academic total synthesis campaign and translates them to a broadly applicable Ag-NP enabled decarboxylative arylation for use in medicinal chemistry. Importantly, this work was enabled by a wide range of key interdisciplinary collaborations spanning material scientists, analytical electrochemists, and medicinal chemists across both academia and industry. Finally, Chapter 4 brings it all together to demonstrate how application of radical-based disconnections can dramatically accelerate access to high value targets.

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

Mode of access: World Wide Web

ISBN: 9798368412306Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

ElectrochemistryIndex Terms--Genre/Form:

542853
Electronic books.

Radical Cross-Coupling Enabled by Functionalized Electrodes.
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520 $a The development of new electrochemical transformations has had a profound impact on the state of organic synthesis. While the use of electrochemistry in organic synthesis dates back several decades, recent efforts to lower the barrier to entry to this technology has allowed to community to embrace this technology more rapidly. These include the development of standardized commercial reactors and a wellspring of educational resources tailored toward synthetic chemists. To this end, our laboratory has sought electrochemical solutions to challenging synthetic problems. Electrochemistry gives the practitioner several unique advantages such as chemoselectivity through control of potential/current, safety by mimicry of harsh chemical reagents, and ease of scalability. Combination of these principles as well as many others that have not been mentioned has brought forth the development of enabling methodology for complex molecule synthesis in the modern age. This doctoral. thesis covers the development of practical C(sp2)-C(sp3) cross-coupling tactics that hinge upon electrode functionalization with silver nanoparticles (Ag-NP). These functionalized electrodes support otherwise challenging Ni-catalytic cross--coupling reactions between activated alkyl carboxylic acids in the form of redox active esters and C(sp2) alkenyl and heteroaryl electrophiles. Chapter 1 provides relevant background on the fundamentals of synthetic organic electrochemistry. Chapter 2 involves the discovery and mechanistic underpinnings of these Ag-NP functionalized electrodes and how their implementation in electrochemical decarboxylative alkenylation can enable a modular platform for terpene synthesis. Chapter 3 takes the key reactivity and mechanistic understandings discovered in the context of an academic total synthesis campaign and translates them to a broadly applicable Ag-NP enabled decarboxylative arylation for use in medicinal chemistry. Importantly, this work was enabled by a wide range of key interdisciplinary collaborations spanning material scientists, analytical electrochemists, and medicinal chemists across both academia and industry. Finally, Chapter 4 brings it all together to demonstrate how application of radical-based disconnections can dramatically accelerate access to high value targets.
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