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Dual Catalysis and the Synthesis of ...

Lam, Heather.

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Dual Catalysis and the Synthesis of Medium-Sized Rings.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Dual Catalysis and the Synthesis of Medium-Sized Rings./
Author:	Lam, Heather.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2020,
Description:	309 p.
Notes:	Source: Dissertations Abstracts International, Volume: 82-06, Section: B.
Contained By:	Dissertations Abstracts International82-06B.
Subject:	Chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28095590
ISBN:	9798698549345

Dual Catalysis and the Synthesis of Medium-Sized Rings.
Lam, Heather.

Dual Catalysis and the Synthesis of Medium-Sized Rings. - Ann Arbor : ProQuest Dissertations & Theses, 2020 - 309 p.

Source: Dissertations Abstracts International, Volume: 82-06, Section: B.

Thesis (Ph.D.)--University of Toronto (Canada), 2020.

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

This thesis describes how the idea of dual catalysis was used to synthesize various heterocyclic scaffolds. Though the initial research plan was for all the projects to involve two distinct catalysts, which is the case for Chapter 1, Chapters 2 and 3 deviate from this original idea where a single catalyst enables two catalytic transformations in a single pot, thus generating efficient methods to synthesize fused heterocyclic scaffolds. The thesis will be divided into three chapters and described as such:Chapter 1 describes a multicatalytic reaction that combines a Rh-catalyzed 1,4-addition and a Pd-catalyzed C-N coupling reaction, which under the appropriate conditions, generates functionalized pyridobenzazepines. Three routes are disclosed to access N-unsubstituted, N-alkylated, and N-arylated products in a one-pot one-step procedure.Chapter 2 describes the optimizations and control studies of a multicatalytic project with the goal to synthesize dibenzothiepines. Originally, it was meant to combine a Cu-catalyzed C-S coupling with a Ni-catalyzed Mizoroki-Heck reaction under the appropriate reaction conditions to generate functionalized dibenzothiepines. We realized that the Ni-catalyst alone could facilitate both a facile C-S coupling as well as the the slower 7-endo selective Heck-reaction. To investigate the mechanism of the reaction, 1H NMR, TEMPO trapping, and EPR studies were performed.Chapter 3 describes an acid-catalyzed (4+3)-cycloaddition between two in situ generated reactive intermediates to access novel oxa-bridged oxazocines. During optimization studies and thorough control studies, it was found that only the organocatalyst was required. The cycloadducts could be ring-opened to access interesting spirocyclic products. Attempts at an enantioselective reaction are reported as well as investigations into the ring-opening reaction of these novel cycloadduct.

ISBN: 9798698549345Subjects--Topical Terms:

516420
Chemistry.
Subjects--Index Terms:

Cycloaddition

Dual Catalysis and the Synthesis of Medium-Sized Rings.
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245 1 0 $a Dual Catalysis and the Synthesis of Medium-Sized Rings.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2020
300 $a 309 p.
500 $a Source: Dissertations Abstracts International, Volume: 82-06, Section: B.
500 $a Advisor: Lautens, Mark.
502 $a Thesis (Ph.D.)--University of Toronto (Canada), 2020.
506 $a This item must not be sold to any third party vendors.
520 $a This thesis describes how the idea of dual catalysis was used to synthesize various heterocyclic scaffolds. Though the initial research plan was for all the projects to involve two distinct catalysts, which is the case for Chapter 1, Chapters 2 and 3 deviate from this original idea where a single catalyst enables two catalytic transformations in a single pot, thus generating efficient methods to synthesize fused heterocyclic scaffolds. The thesis will be divided into three chapters and described as such:Chapter 1 describes a multicatalytic reaction that combines a Rh-catalyzed 1,4-addition and a Pd-catalyzed C-N coupling reaction, which under the appropriate conditions, generates functionalized pyridobenzazepines. Three routes are disclosed to access N-unsubstituted, N-alkylated, and N-arylated products in a one-pot one-step procedure.Chapter 2 describes the optimizations and control studies of a multicatalytic project with the goal to synthesize dibenzothiepines. Originally, it was meant to combine a Cu-catalyzed C-S coupling with a Ni-catalyzed Mizoroki-Heck reaction under the appropriate reaction conditions to generate functionalized dibenzothiepines. We realized that the Ni-catalyst alone could facilitate both a facile C-S coupling as well as the the slower 7-endo selective Heck-reaction. To investigate the mechanism of the reaction, 1H NMR, TEMPO trapping, and EPR studies were performed.Chapter 3 describes an acid-catalyzed (4+3)-cycloaddition between two in situ generated reactive intermediates to access novel oxa-bridged oxazocines. During optimization studies and thorough control studies, it was found that only the organocatalyst was required. The cycloadducts could be ring-opened to access interesting spirocyclic products. Attempts at an enantioselective reaction are reported as well as investigations into the ring-opening reaction of these novel cycloadduct.
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653 $a Nickel
653 $a Palladium
653 $a Rhodium
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