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Main Group-Catalyzed Carbon to Carbo...

Bagdasarian, Alex Levon.

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Main Group-Catalyzed Carbon to Carbon Bond-Forming Reactions of Dicoordinate Carbocations.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Main Group-Catalyzed Carbon to Carbon Bond-Forming Reactions of Dicoordinate Carbocations./
Author:	Bagdasarian, Alex Levon.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2019,
Description:	335 p.
Notes:	Source: Dissertations Abstracts International, Volume: 81-08, Section: B.
Contained By:	Dissertations Abstracts International81-08B.
Subject:	Organic chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=27670212
ISBN:	9781392750896

Main Group-Catalyzed Carbon to Carbon Bond-Forming Reactions of Dicoordinate Carbocations.
Bagdasarian, Alex Levon.

Main Group-Catalyzed Carbon to Carbon Bond-Forming Reactions of Dicoordinate Carbocations. - Ann Arbor : ProQuest Dissertations & Theses, 2019 - 335 p.

Source: Dissertations Abstracts International, Volume: 81-08, Section: B.

Thesis (Ph.D.)--University of California, Los Angeles, 2019.

This item is not available from ProQuest Dissertations & Theses.

This dissertation focuses on the development of catalytic Carbon to Carbon (C-C) bond forming reactions of dicoordinate carbocations. The unique reactivity described herein focuses on the use of ionizable groups and appropriate counter anions to facilitate productive reactions of high-energy cationic intermediates. The first chapter discusses the exploration of phenyl carbocations, generated from aryl fluorides under silylium-weakly coordinating anion (WCA) catalysis, in the context of hydrocarbon functionalization. Chapter two describes the discovery of C-H insertion and reductive Friedel-Crafts reactions of vinyl carbocations generated from vinyl triflates and silylium-WCA salts. Chapter three describes a novel approach to generating vinyl cations using Lithium Lewis acids. Interestingly, these vinyl carbocations are formed under basic conditions, with lithium hexamethyldisilazide (LiHMDS) as the Lewis acid precursor. Chapter four describes two new catalytic manifolds using urea-based organocatalysts. In one instance, the urea catalyst directly ionizes the vinyl triflate through a hydrogen-bonding interaction to promote intra molecular C-H insertion reactions. In another case, urea organocatalysts combined with LiHMDS, result in novel lithium-urea catalyst that promote Friedel-Crafts reactions of vinyl triflates. In summary, these studies have resulted in the development of new catalytic methods using main-group catalysis for the formation of C-C bonds.

ISBN: 9781392750896Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Carbon to carbon bonds

Main Group-Catalyzed Carbon to Carbon Bond-Forming Reactions of Dicoordinate Carbocations.
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245 1 0 $a Main Group-Catalyzed Carbon to Carbon Bond-Forming Reactions of Dicoordinate Carbocations.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2019
300 $a 335 p.
500 $a Source: Dissertations Abstracts International, Volume: 81-08, Section: B.
500 $a Advisor: Nelson, Hosea Martin.
502 $a Thesis (Ph.D.)--University of California, Los Angeles, 2019.
506 $a This item is not available from ProQuest Dissertations & Theses.
506 $a This item must not be sold to any third party vendors.
520 $a This dissertation focuses on the development of catalytic Carbon to Carbon (C-C) bond forming reactions of dicoordinate carbocations. The unique reactivity described herein focuses on the use of ionizable groups and appropriate counter anions to facilitate productive reactions of high-energy cationic intermediates. The first chapter discusses the exploration of phenyl carbocations, generated from aryl fluorides under silylium-weakly coordinating anion (WCA) catalysis, in the context of hydrocarbon functionalization. Chapter two describes the discovery of C-H insertion and reductive Friedel-Crafts reactions of vinyl carbocations generated from vinyl triflates and silylium-WCA salts. Chapter three describes a novel approach to generating vinyl cations using Lithium Lewis acids. Interestingly, these vinyl carbocations are formed under basic conditions, with lithium hexamethyldisilazide (LiHMDS) as the Lewis acid precursor. Chapter four describes two new catalytic manifolds using urea-based organocatalysts. In one instance, the urea catalyst directly ionizes the vinyl triflate through a hydrogen-bonding interaction to promote intra molecular C-H insertion reactions. In another case, urea organocatalysts combined with LiHMDS, result in novel lithium-urea catalyst that promote Friedel-Crafts reactions of vinyl triflates. In summary, these studies have resulted in the development of new catalytic methods using main-group catalysis for the formation of C-C bonds.
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653 $a Carbocations
653 $a Weakly coordinating anion
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