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Lewis and Bronsted Acidic Homogeneou...

Gudz, Anton L.

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Lewis and Bronsted Acidic Homogeneous Catalysis for C-O Bond Reduction and Late-Stage Natural Product Functionalization.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Lewis and Bronsted Acidic Homogeneous Catalysis for C-O Bond Reduction and Late-Stage Natural Product Functionalization./
Author:	Gudz, Anton L.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2020,
Description:	242 p.
Notes:	Source: Dissertations Abstracts International, Volume: 82-03, Section: B.
Contained By:	Dissertations Abstracts International82-03B.
Subject:	Inorganic chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=27995661
ISBN:	9798664725810

Lewis and Bronsted Acidic Homogeneous Catalysis for C-O Bond Reduction and Late-Stage Natural Product Functionalization.
Gudz, Anton L.

Lewis and Bronsted Acidic Homogeneous Catalysis for C-O Bond Reduction and Late-Stage Natural Product Functionalization. - Ann Arbor : ProQuest Dissertations & Theses, 2020 - 242 p.

Source: Dissertations Abstracts International, Volume: 82-03, Section: B.

Thesis (Ph.D.)--The University of North Carolina at Chapel Hill, 2020.

This item must not be sold to any third party vendors.

Diminishing fossil fuel resources and growing environmental concerns require the development of alternative methods for sustainable production of fine chemicals and pharmaceutically relevant compounds. Biomass and natural product resources constitute a large reservoir of organic carbon (C-O bonds) that can be converted into commodity chemicals or drug candidates on an industrially applicable scale. This dissertation aims to explore various homogeneous catalytic methods that help attain this goal.The main objective of this work is to add to the existing methodology in the field of selective catalytic C-O bond reductions. Due to the complex regio- and chemoselectivities associated with these reactions, it is difficult to design and control such systems. In this vein, several Lewis and Bronsted acidic homogenous catalysts have emerged to allow for C-O bond reduction, and often subsequent generation of structural complexity.The first half of this dissertation explores the fundamental reactivity of existing boron-based systems, specifically studying tris(pentafluorophenyl)borane B(C6F5)3 as the primary workhorse catalyst. Silyl-phosphonium ions are explored as new silylium ion carriers in the modified Piers hydrosilylation catalytic cycle. This adds depth to the existing pool of knowledge, providing alternatives for chemoselective C-O bond reductions.The second half of this work pushes the boundaries of late-stage natural product functionalization field by exploring catalytic methods to discover new molecules. Bioactive natural products are used extensively with Lewis and Bronsted acids and nucleophiles to generate previously unreported molecular scaffolds. These new structures likely possess biological activity different from their parent molecules, making them ideal early candidates for biological assays.Ultimately, the results presented benefit both the synthetic inorganic and organic catalysis communities, as well as the biological and pharmaceutical chemists studying natural products as potential drug candidates.

ISBN: 9798664725810Subjects--Topical Terms:

3173556
Inorganic chemistry.
Subjects--Index Terms:

Biomass

Lewis and Bronsted Acidic Homogeneous Catalysis for C-O Bond Reduction and Late-Stage Natural Product Functionalization.
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245 1 0 $a Lewis and Bronsted Acidic Homogeneous Catalysis for C-O Bond Reduction and Late-Stage Natural Product Functionalization.
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500 $a Source: Dissertations Abstracts International, Volume: 82-03, Section: B.
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502 $a Thesis (Ph.D.)--The University of North Carolina at Chapel Hill, 2020.
506 $a This item must not be sold to any third party vendors.
520 $a Diminishing fossil fuel resources and growing environmental concerns require the development of alternative methods for sustainable production of fine chemicals and pharmaceutically relevant compounds. Biomass and natural product resources constitute a large reservoir of organic carbon (C-O bonds) that can be converted into commodity chemicals or drug candidates on an industrially applicable scale. This dissertation aims to explore various homogeneous catalytic methods that help attain this goal.The main objective of this work is to add to the existing methodology in the field of selective catalytic C-O bond reductions. Due to the complex regio- and chemoselectivities associated with these reactions, it is difficult to design and control such systems. In this vein, several Lewis and Bronsted acidic homogenous catalysts have emerged to allow for C-O bond reduction, and often subsequent generation of structural complexity.The first half of this dissertation explores the fundamental reactivity of existing boron-based systems, specifically studying tris(pentafluorophenyl)borane B(C6F5)3 as the primary workhorse catalyst. Silyl-phosphonium ions are explored as new silylium ion carriers in the modified Piers hydrosilylation catalytic cycle. This adds depth to the existing pool of knowledge, providing alternatives for chemoselective C-O bond reductions.The second half of this work pushes the boundaries of late-stage natural product functionalization field by exploring catalytic methods to discover new molecules. Bioactive natural products are used extensively with Lewis and Bronsted acids and nucleophiles to generate previously unreported molecular scaffolds. These new structures likely possess biological activity different from their parent molecules, making them ideal early candidates for biological assays.Ultimately, the results presented benefit both the synthetic inorganic and organic catalysis communities, as well as the biological and pharmaceutical chemists studying natural products as potential drug candidates.
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