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Unlocking New Odd-Electron Pathways via Photoactive Catalysis.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Unlocking New Odd-Electron Pathways via Photoactive Catalysis./
Author:	Polites, Viktor Christian.
Description:	1 online resource (397 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 84-02, Section: B.
Contained By:	Dissertations Abstracts International84-02B.
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=29162764click for full text (PQDT)
ISBN:	9798837517198

Unlocking New Odd-Electron Pathways via Photoactive Catalysis.
Polites, Viktor Christian.

Unlocking New Odd-Electron Pathways via Photoactive Catalysis. - 1 online resource (397 pages)

Source: Dissertations Abstracts International, Volume: 84-02, Section: B.

Thesis (Ph.D.)--University of Pennsylvania, 2022.

Includes bibliographical references

In the past decade, renewed interest in odd-electron pathways has reaffirmed organic chemistry's indispensable role in the synthesis of complex molecules and in drug-discovery efforts. Odd-electron intermediates unlock reactivity patterns that are not observed in two-electron processes and offer complementary chemoselectivity. Importantly, these processes are often "blind" to the source of radical and can thus be adapted toward a diverse array of chemical feedstocks. Photoredox catalysis harnesses radicals in a controlled, predicable manner and can be used to orchestrate elaborate radical and polar bond-forming processes, which allowed the development of the radical-polar crossover annulation reaction (RPAR) paradigm. Furthermore, these catalysts, in conjunction with transition metal complexes, enable multiple C-C bond-forming events in so-called dicarbofunctionalization (DCF) reactions, and can even be used to functionalize commodity materials via photochemical C-H abstraction. Visible light can also be used to excite electron donor-acceptor complexes in the absence of a photocatalyst to permit radical generation. This mode of reactivity has provided an avenue to new bioisosteric space via the late-stage introduction of bicyclo[1.1.1]pentyl (BCP) motifs. Finally, photochemically-initiated hydrogen-atom transfer (HAT) catalysis can be harnessed to access strong single-electron reductants that permit the single C-F bond activation of trifluoroacetates and -acetamides. This has allowed facile access to gem-difluoromethylene containing compounds that are challenging to prepare by state-of-the-art methods. Discoveries in each of these arenas will be discussed.

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

Mode of access: World Wide Web

ISBN: 9798837517198Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Cross-couplingIndex Terms--Genre/Form:

542853
Electronic books.

Unlocking New Odd-Electron Pathways via Photoactive Catalysis.
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245 1 0 $a Unlocking New Odd-Electron Pathways via Photoactive Catalysis.
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500 $a Source: Dissertations Abstracts International, Volume: 84-02, Section: B.
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502 $a Thesis (Ph.D.)--University of Pennsylvania, 2022.
504 $a Includes bibliographical references
520 $a In the past decade, renewed interest in odd-electron pathways has reaffirmed organic chemistry's indispensable role in the synthesis of complex molecules and in drug-discovery efforts. Odd-electron intermediates unlock reactivity patterns that are not observed in two-electron processes and offer complementary chemoselectivity. Importantly, these processes are often "blind" to the source of radical and can thus be adapted toward a diverse array of chemical feedstocks. Photoredox catalysis harnesses radicals in a controlled, predicable manner and can be used to orchestrate elaborate radical and polar bond-forming processes, which allowed the development of the radical-polar crossover annulation reaction (RPAR) paradigm. Furthermore, these catalysts, in conjunction with transition metal complexes, enable multiple C-C bond-forming events in so-called dicarbofunctionalization (DCF) reactions, and can even be used to functionalize commodity materials via photochemical C-H abstraction. Visible light can also be used to excite electron donor-acceptor complexes in the absence of a photocatalyst to permit radical generation. This mode of reactivity has provided an avenue to new bioisosteric space via the late-stage introduction of bicyclo[1.1.1]pentyl (BCP) motifs. Finally, photochemically-initiated hydrogen-atom transfer (HAT) catalysis can be harnessed to access strong single-electron reductants that permit the single C-F bond activation of trifluoroacetates and -acetamides. This has allowed facile access to gem-difluoromethylene containing compounds that are challenging to prepare by state-of-the-art methods. Discoveries in each of these arenas will be discussed.
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653 $a Fluoride activation
653 $a Nickel catalysis
653 $a Photoredox catalysis
653 $a Radical-polar crossover
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