東華大學圖書館 |

Language: English

Help

回圖書館首頁

手機版館藏查詢

Back to Search results for [ null ]

Switch To: Labeled | MARC Mode | ISBD

Controlled α-Halogenation of Alkyl S...

Penn, Kyle Robert.

Linked to FindBook

Google Book

Amazon

博客來

Controlled α-Halogenation of Alkyl Sulfonamides and Development of Highly Active Bifunctional (Benz)Imidazolyl-Palladium Catalysts for Application in Sustainable Cross-Coupling Reactions.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Controlled α-Halogenation of Alkyl Sulfonamides and Development of Highly Active Bifunctional (Benz)Imidazolyl-Palladium Catalysts for Application in Sustainable Cross-Coupling Reactions./
Author:	Penn, Kyle Robert.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2023,
Description:	132 p.
Notes:	Source: Dissertations Abstracts International, Volume: 85-04, Section: B.
Contained By:	Dissertations Abstracts International85-04B.
Subject:	Acids. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30615851
ISBN:	9798380484107

Controlled α-Halogenation of Alkyl Sulfonamides and Development of Highly Active Bifunctional (Benz)Imidazolyl-Palladium Catalysts for Application in Sustainable Cross-Coupling Reactions.
Penn, Kyle Robert.

Controlled α-Halogenation of Alkyl Sulfonamides and Development of Highly Active Bifunctional (Benz)Imidazolyl-Palladium Catalysts for Application in Sustainable Cross-Coupling Reactions. - Ann Arbor : ProQuest Dissertations & Theses, 2023 - 132 p.

Source: Dissertations Abstracts International, Volume: 85-04, Section: B.

Thesis (Ph.D.)--North Carolina State University, 2023.

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

Transition-metal-catalyzed cross-coupling reactions are some of the most valuable and synthetically productive steps in the formation of organic compounds and materials relevant to an array of chemical industries. The Suzuki-Miyaura Coupling (SMC) specifically, is the single most commonly used carbon-carbon bond forming reaction in the pharmaceutical industry. Historically, improvements in Suzuki-Miyaura coupling reactions have often been accomplished by increasing the reactivity and stability of the metal catalysts by use of increasingly more effective ligands. In this work, a family of air- and moisture-stable dinuclear 2- benzimidazolylpalladium complexes, known to act as highly active bifunctional catalysts for sustainable cross-coupling reactions, is expanded upon and structure-activity relationships are studied and defined with respect to the catalysts' performance in Suzuki-Miyaura Coupling (SMC) reactions. New understanding of structure-activity trends is leveraged to develop a more active catalyst capable of catalyzing the Suzuki coupling of aryl bromides as well as aryl chlorides efficiently and with good functional group compatibility in alcohol solvents at catalyst loadings of 0.003 mol% (60 ppm Pd) for aryl bromides and as low as 0.1 mol% (2000 ppm Pd) for aryl chlorides.Bis(azolium)dichloride salts constitute stable and convenient precursors for metal bis(carbenes) as ligands for a wide range of metal-catalyzed processes. However, the synthesis of such salts is often inefficient in part due to the low reactivity of dichloroalkanes in nucleophilic substitution reactions. New reaction kinetics and mechanistic studies in the literature on pyridine derivatives have inspired us to develop a novel method for the improved synthesis of bis(azolium) chloride salts in excellent yields, applicable to a wide scope of heterocyclic cores. This method can also be applied to the direct synthesis of bis(NHC)-metal complexes in a one-pot reaction from imidazole derivatives.The sulfonamide functional group has many unique factors that can be leveraged for drug design, and some biologically relevant sulfonamide-containing compounds have been accessed from α-halogenated sulfonamide derivatives. However, synthesis of such derivatives is often difficult due to unselective polyhalogenation, often creating inseparable mixtures of product when base-mediated halogenation is attempted. In this work we developed new methods to selectively access these α-halogenated derivatives directly from alkyl sulfonamides.

ISBN: 9798380484107Subjects--Topical Terms:

922327
Acids.

Controlled α-Halogenation of Alkyl Sulfonamides and Development of Highly Active Bifunctional (Benz)Imidazolyl-Palladium Catalysts for Application in Sustainable Cross-Coupling Reactions.
LDR:03915nmm a2200385 4500 001 2393990
005 20240414211941.5
006 m o d
007 cr#unu||||||||
008 251215s2023 ||||||||||||||||| ||eng d
020 $a 9798380484107
035 $a (MiAaPQ)AAI30615851
035 $a (MiAaPQ)NCState_Univ18402041017
035 $a AAI30615851
040 $a MiAaPQ $c MiAaPQ
100 1 $a Penn, Kyle Robert. $3 3763474
245 1 0 $a Controlled α-Halogenation of Alkyl Sulfonamides and Development of Highly Active Bifunctional (Benz)Imidazolyl-Palladium Catalysts for Application in Sustainable Cross-Coupling Reactions.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2023
300 $a 132 p.
500 $a Source: Dissertations Abstracts International, Volume: 85-04, Section: B.
500 $a Advisor: Lindsay, Vincent;Lindsey, Jonathan S.;Proulx, Caroline;Pierce, Joshua G.;Heugten, Kimberly Ange-Van.
502 $a Thesis (Ph.D.)--North Carolina State University, 2023.
506 $a This item must not be sold to any third party vendors.
520 $a Transition-metal-catalyzed cross-coupling reactions are some of the most valuable and synthetically productive steps in the formation of organic compounds and materials relevant to an array of chemical industries. The Suzuki-Miyaura Coupling (SMC) specifically, is the single most commonly used carbon-carbon bond forming reaction in the pharmaceutical industry. Historically, improvements in Suzuki-Miyaura coupling reactions have often been accomplished by increasing the reactivity and stability of the metal catalysts by use of increasingly more effective ligands. In this work, a family of air- and moisture-stable dinuclear 2- benzimidazolylpalladium complexes, known to act as highly active bifunctional catalysts for sustainable cross-coupling reactions, is expanded upon and structure-activity relationships are studied and defined with respect to the catalysts' performance in Suzuki-Miyaura Coupling (SMC) reactions. New understanding of structure-activity trends is leveraged to develop a more active catalyst capable of catalyzing the Suzuki coupling of aryl bromides as well as aryl chlorides efficiently and with good functional group compatibility in alcohol solvents at catalyst loadings of 0.003 mol% (60 ppm Pd) for aryl bromides and as low as 0.1 mol% (2000 ppm Pd) for aryl chlorides.Bis(azolium)dichloride salts constitute stable and convenient precursors for metal bis(carbenes) as ligands for a wide range of metal-catalyzed processes. However, the synthesis of such salts is often inefficient in part due to the low reactivity of dichloroalkanes in nucleophilic substitution reactions. New reaction kinetics and mechanistic studies in the literature on pyridine derivatives have inspired us to develop a novel method for the improved synthesis of bis(azolium) chloride salts in excellent yields, applicable to a wide scope of heterocyclic cores. This method can also be applied to the direct synthesis of bis(NHC)-metal complexes in a one-pot reaction from imidazole derivatives.The sulfonamide functional group has many unique factors that can be leveraged for drug design, and some biologically relevant sulfonamide-containing compounds have been accessed from α-halogenated sulfonamide derivatives. However, synthesis of such derivatives is often difficult due to unselective polyhalogenation, often creating inseparable mixtures of product when base-mediated halogenation is attempted. In this work we developed new methods to selectively access these α-halogenated derivatives directly from alkyl sulfonamides.
590 $a School code: 0155.
650 4 $a Acids. $3 922327
650 4 $a Reagents. $3 3683752
650 4 $a Palladium. $3 644757
650 4 $a Nuclear magnetic resonance--NMR. $3 3560258
650 4 $a Decomposition. $3 3561186
650 4 $a Fluorides. $3 620981
650 4 $a Chromatography. $3 1073639
650 4 $a Potassium. $3 3562093
650 4 $a Lithium. $3 1638490
650 4 $a Nitrogen. $3 1314426
650 4 $a Chloride. $3 3681736
650 4 $a Iodine. $3 2147588
650 4 $a Sodium. $3 3562677
650 4 $a Carbon. $3 604057
650 4 $a Solvents. $3 620946
650 4 $a Sustainability. $3 1029978
650 4 $a Flexibility. $3 3560705
650 4 $a Alcohol. $3 872287
650 4 $a Chemical bonds. $3 560512
650 4 $a Catalysis. $3 560465
650 4 $a Polyethylene glycol. $3 3686750
650 4 $a Chemistry. $3 516420
650 4 $a Medical imaging. $3 3172799
650 4 $a Pharmaceutical sciences. $3 3173021
650 4 $a Plastics. $3 649803
650 4 $a Polymer chemistry. $3 3173488
690 $a 0640
690 $a 0485
690 $a 0574
690 $a 0572
690 $a 0795
690 $a 0495
710 2 $a North Carolina State University. $3 1018772
773 0 $t Dissertations Abstracts International $g 85-04B.
790 $a 0155
791 $a Ph.D.
792 $a 2023
793 $a English
856 4 0 $u https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30615851