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Photocatalyzed Methods for the Construction of Csp3 Bonds / Anasheh Sookezian.

Dissertations & Theses @ University of Pennsylvania Available online

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Format:
Book
Thesis/Dissertation
Author/Creator:
Sookezian, Anasheh, author.
Contributor:
University of Pennsylvania. Chemistry, degree granting institution.
Language:
English
Subjects (All):
Organic chemistry.
Physical chemistry.
Pharmaceutical sciences.
Chemistry--Penn dissertations.
Penn dissertations--Chemistry.
Local Subjects:
Organic chemistry.
Physical chemistry.
Pharmaceutical sciences.
Chemistry--Penn dissertations.
Penn dissertations--Chemistry.
Physical Description:
1 online resource (161 pages)
Contained In:
Dissertations Abstracts International 85-01B.
Place of Publication:
[Philadelphia, Pennsylvania] : University of Pennsylvania, 2022.
Ann Arbor : ProQuest Dissertations & Theses, 2023
Language Note:
English
Summary:
Analysis of historical data in the pharmaceutical industry has shown a positive correlation between Fsp3 (the fraction of a molecule with sp3 hybridized bonds) and clinical success. With increased interest in the synthesis of compounds with higher Fsp3 , there has been a renewed interest in the broader chemistry community in methods for the installation of these saturated moieties. However, formation as well as functionalization of Csp3 bonds represent some of the most challenging transformations in organic chemistry. Visible light-mediated transformations have become increasingly more popular in recent years as a tool for the formation of these difficult bonds. Photochemistry offers a mild approach to the formation and utilization of alkyl radicals in a wide range of settings, affording a broad range of possible products. Firstly, photoredox catalysis harnesses radicals in a controlled, predicable manner and can be used to orchestrate elaborate radical and polar bond-forming processes, allowing for the development of radical-polar crossover (RPC) reactions. Herein, two separate RPC reactions are explored: a dicarbofunctionalization reaction, furnishing complex carbon skeleton frameworks, as well as a carbo-sulfamoylation reaction, furnishing pharmaceutically relevant alkyl sulfonamide moieties. Furthermore, metallaphotoredox, also known as photoredox/nickel dual catalysis, can be used to develop a wide array of cross-coupling chemistry. Through the use of thianthrenium salts as a new handle for functionalization, dual catalysis approaches to the alkylation and aminomethylation of these salts are explored herein.
Notes:
Source: Dissertations Abstracts International, Volume: 85-01, Section: B.
Advisors: Molander, Gary A.; Committee members: Chenoweth, David M.; Huryn, Donna M.; Matthews, Megan L.
Department: Chemistry.
Ph.D. University of Pennsylvania 2023.
Local Notes:
School code: 0175
ISBN:
9798379753511
Access Restriction:
Restricted for use by site license.
This item is not available from ProQuest Dissertations & Theses.

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