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Applications of Boronic Acids, Boron...

Manhas, Sanjay.

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Applications of Boronic Acids, Boronates, and Borates as Catalysts or Promoters for Chemical Transformations.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Applications of Boronic Acids, Boronates, and Borates as Catalysts or Promoters for Chemical Transformations./
Author:	Manhas, Sanjay.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
Description:	459 p.
Notes:	Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.
Contained By:	Dissertation Abstracts International79-12B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10688007
ISBN:	9780438186620

Applications of Boronic Acids, Boronates, and Borates as Catalysts or Promoters for Chemical Transformations.
Manhas, Sanjay.

Applications of Boronic Acids, Boronates, and Borates as Catalysts or Promoters for Chemical Transformations. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 459 p.

Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.

Thesis (Ph.D.)--University of Toronto (Canada), 2018.

The central theme of the research outlined in this thesis is to develop synthetic applications of organoboron compounds as catalysts or promoters. Chapter 1 emphasizes the physical properties of boronic acids and borates. Relevant applications that exploit boronic acid Lewis acidity and the ability to form reversible covalent interactions with alcohols and carboxylic acids are reviewed. In chapter 2, boron-based Lewis acid- and Bronsted acid-catalyzed Fischer glycosidations were explored. In this study, protected C-(1)-hemiacetal sugars were activated towards O- and S -glycosidations with boronic esters and borates. Chapter 3 describes our efforts towards an efficient protecting group free Fischer glycosidation under mild conditions. In this study, boronic acids were used as transient protecting groups and phase-transfer reagents for sugars in low-polarity solvents. We also found that the binding of boronic acids to free sugars changed the thermodynamic profile of the Fischer glycosidation. In chapter 4 we report a method for protodeboronation of electron-neutral and electron-rich arylboronic acids with electron-deficient beta-hydroxy acids and mildly acidic additives. Calculated transition state energies supported the experimentally observed trends for the protodeboronation of arylboronic acids. Finally, progress was made towards extending the protodeboronation protocol to deuterodeboronations of arylboronic acids.

ISBN: 9780438186620Subjects--Topical Terms:

523952
Organic chemistry.

Applications of Boronic Acids, Boronates, and Borates as Catalysts or Promoters for Chemical Transformations.
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520 $a The central theme of the research outlined in this thesis is to develop synthetic applications of organoboron compounds as catalysts or promoters. Chapter 1 emphasizes the physical properties of boronic acids and borates. Relevant applications that exploit boronic acid Lewis acidity and the ability to form reversible covalent interactions with alcohols and carboxylic acids are reviewed. In chapter 2, boron-based Lewis acid- and Bronsted acid-catalyzed Fischer glycosidations were explored. In this study, protected C-(1)-hemiacetal sugars were activated towards O- and S -glycosidations with boronic esters and borates. Chapter 3 describes our efforts towards an efficient protecting group free Fischer glycosidation under mild conditions. In this study, boronic acids were used as transient protecting groups and phase-transfer reagents for sugars in low-polarity solvents. We also found that the binding of boronic acids to free sugars changed the thermodynamic profile of the Fischer glycosidation. In chapter 4 we report a method for protodeboronation of electron-neutral and electron-rich arylboronic acids with electron-deficient beta-hydroxy acids and mildly acidic additives. Calculated transition state energies supported the experimentally observed trends for the protodeboronation of arylboronic acids. Finally, progress was made towards extending the protodeboronation protocol to deuterodeboronations of arylboronic acids.
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