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Charge-Enhanced Organocatalysts: Synthesis and Application toward Symmetric and Asymmetric Reactions.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Charge-Enhanced Organocatalysts: Synthesis and Application toward Symmetric and Asymmetric Reactions.
Author:	Riegel, George Frederic, IV.
Published:	Ann Arbor : ProQuest Dissertations & Theses, 2022
Description:	315 p.
Notes:	Source: Dissertations Abstracts International, Volume: 84-03, Section: B.
Notes:	Advisor: Kass, Steven R.
Contained By:	Dissertations Abstracts International84-03B.
Subject:	Chemistry.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28964519
ISBN:	9798845407627

Charge-Enhanced Organocatalysts: Synthesis and Application toward Symmetric and Asymmetric Reactions.
Riegel, George Frederic, IV.

Charge-Enhanced Organocatalysts: Synthesis and Application toward Symmetric and Asymmetric Reactions. - Ann Arbor : ProQuest Dissertations & Theses, 2022 - 315 p.

Source: Dissertations Abstracts International, Volume: 84-03, Section: B.

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

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

Hydrogen bonds are ubiquitous in Nature and are the principal interaction through which enzymes catalyze reactions. Bronsted acid organocatalysts mimic this process and present a greener alternative to metal-based species as the former do not contribute to the consumption of limited metal resources or the production of toxic metal wastes. Despite these benefits, organocatalysts have remained underutilized in industrial processes because they typically have low activity compared to their inorganic counterparts. In 2015, the Kass group demonstrated that Bronsted acidity and organocatalytic activity could be significantly enhanced in low-polarity media through the incorporation of formal positive charges. This principle has since been extended to common organocatalyst scaffolds such as thioureas and phosphoric acids. This dissertation details the further enhancement of Bronsted acidity in low-polarity solvents by the concerted action of positive charges and electron-withdrawing groups and a study on the implications of catalyst acidity on the rate of Friedel–Crafts alkylation reactions. In addition, the interactions of charged thioureas and Bronsted acidic co-catalysts are explored and the charge-enhanced acidity approach is extended to asymmetric TADDOL organocatalysis.

ISBN: 9798845407627Subjects--Topical Terms:

188628
Chemistry.
Subjects--Index Terms:

Bronsted acid catalysis

Charge-Enhanced Organocatalysts: Synthesis and Application toward Symmetric and Asymmetric Reactions.
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245 1 0 $a Charge-Enhanced Organocatalysts: Synthesis and Application toward Symmetric and Asymmetric Reactions.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2022
300 $a 315 p.
500 $a Source: Dissertations Abstracts International, Volume: 84-03, Section: B.
500 $a Advisor: Kass, Steven R.
502 $a Thesis (Ph.D.)--University of Minnesota, 2022.
506 $a This item must not be sold to any third party vendors.
520 $a Hydrogen bonds are ubiquitous in Nature and are the principal interaction through which enzymes catalyze reactions. Bronsted acid organocatalysts mimic this process and present a greener alternative to metal-based species as the former do not contribute to the consumption of limited metal resources or the production of toxic metal wastes. Despite these benefits, organocatalysts have remained underutilized in industrial processes because they typically have low activity compared to their inorganic counterparts. In 2015, the Kass group demonstrated that Bronsted acidity and organocatalytic activity could be significantly enhanced in low-polarity media through the incorporation of formal positive charges. This principle has since been extended to common organocatalyst scaffolds such as thioureas and phosphoric acids. This dissertation details the further enhancement of Bronsted acidity in low-polarity solvents by the concerted action of positive charges and electron-withdrawing groups and a study on the implications of catalyst acidity on the rate of Friedel–Crafts alkylation reactions. In addition, the interactions of charged thioureas and Bronsted acidic co-catalysts are explored and the charge-enhanced acidity approach is extended to asymmetric TADDOL organocatalysis.
590 $a School code: 0130.
650 4 $a Chemistry. $3 188628
650 4 $a Organic chemistry. $3 708640
653 $a Bronsted acid catalysis
653 $a Metal-free catalyst
653 $a Organocatalysis
653 $a Recyclable catalyst
653 $a TADDOL
653 $a Thiourea
690 $a 0485
690 $a 0490
710 2 $a University of Minnesota. $b Chemistry. $3 730277
773 0 $t Dissertations Abstracts International $g 84-03B.
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793 $a English
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