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Tong, Xiaoyu Dan,

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Novel Reactivity and Applications of Transition Metal-Catalyzed Nucleophilic Substitution Reactions /

Record Type:	Electronic resources : Monograph/item
Title/Author:	Novel Reactivity and Applications of Transition Metal-Catalyzed Nucleophilic Substitution Reactions // Xiaoyu Dan Tong.
Author:	Tong, Xiaoyu Dan,
Description:	1 electronic resource (236 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 86-03, Section: B.
Contained By:	Dissertations Abstracts International86-03B.
Subject:	Metals. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=31466333
ISBN:	9798384345589

Novel Reactivity and Applications of Transition Metal-Catalyzed Nucleophilic Substitution Reactions /
Tong, Xiaoyu Dan,

Novel Reactivity and Applications of Transition Metal-Catalyzed Nucleophilic Substitution Reactions /Xiaoyu Dan Tong. - 1 electronic resource (236 pages)

Source: Dissertations Abstracts International, Volume: 86-03, Section: B.

For more than 20 years, the Fu lab has explored the use of transition metal catalysts to enable novel nucleophilic substitution reactions. However, deficiencies in both fundamental reactivity and useful applications persist in this area. The research detailed in this thesis focuses on the development of reactivity and applications of transition metal-catalyzed nucleophilic substitution reactions.Chapter 2 recounts the development of the nickel-catalyzed enantioconvergent alkylation reaction of racemic α-zincated amides with unactivated alkyl electrophile. This method constitutes a new example of the use of racemic nucleophiles in asymmetric cross-coupling reaction. It also addresses the long-standing challenge of controlling the absolute stereochemistry in the alkylation reaction between enolates and unactivated electrophiles. The reaction takes place under mild conditions. The products of this reaction are conveniently transformed into a range of chiral organic compounds. Taking advantage of a wide array of techniques, we have studied the mechanism of the reaction. Specifically, we determined and structurally characterized the predominant nickel-containing species during the reaction. Strong experimental support was obtained for the mechanism by which the electrophile is engaged in the reaction.Chapter 3 describes the conception, discovery, optimization, and application of a nickelcatalyzed enantioconvergent arylation of racemic cyclic electrophiles-namely, 3-halopyrrolidines. We tackled the difficulties associated with the use of this highly challenging class of substrates via extensive ligand optimization and the application of design of experiments. After the reaction scope was explored, we applied it towards the expedient synthesis of an array of bioactive pyrrolidines that previously involved long and inefficient routes.Chapter 4 includes the development of the first iron-catalyzed cross-coupling reaction in the Fu lab-the reductive cross-coupling reaction of readily available olefins with unactivated 1° alkyl electrophiles, including the discovery of the surprising effect of a magnesium salt, substrate scope, and preliminary mechanistic study. Additionally, at the end of this chapter, efforts towards the optimization of an iron-catalyzed reductive cross-coupling reaction of olefins with 2° alkyl electrophiles are reported. The effects of ligands are examined in detail.Chapter 5 outlines the discovery and optimization of a novel copper-catalyzed asymmetric alkylation reaction of a variety of nucleophiles.

English

ISBN: 9798384345589Subjects--Topical Terms:

601053
Metals.

Novel Reactivity and Applications of Transition Metal-Catalyzed Nucleophilic Substitution Reactions /
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520 $a For more than 20 years, the Fu lab has explored the use of transition metal catalysts to enable novel nucleophilic substitution reactions. However, deficiencies in both fundamental reactivity and useful applications persist in this area. The research detailed in this thesis focuses on the development of reactivity and applications of transition metal-catalyzed nucleophilic substitution reactions.Chapter 2 recounts the development of the nickel-catalyzed enantioconvergent alkylation reaction of racemic α-zincated amides with unactivated alkyl electrophile. This method constitutes a new example of the use of racemic nucleophiles in asymmetric cross-coupling reaction. It also addresses the long-standing challenge of controlling the absolute stereochemistry in the alkylation reaction between enolates and unactivated electrophiles. The reaction takes place under mild conditions. The products of this reaction are conveniently transformed into a range of chiral organic compounds. Taking advantage of a wide array of techniques, we have studied the mechanism of the reaction. Specifically, we determined and structurally characterized the predominant nickel-containing species during the reaction. Strong experimental support was obtained for the mechanism by which the electrophile is engaged in the reaction.Chapter 3 describes the conception, discovery, optimization, and application of a nickelcatalyzed enantioconvergent arylation of racemic cyclic electrophiles-namely, 3-halopyrrolidines. We tackled the difficulties associated with the use of this highly challenging class of substrates via extensive ligand optimization and the application of design of experiments. After the reaction scope was explored, we applied it towards the expedient synthesis of an array of bioactive pyrrolidines that previously involved long and inefficient routes.Chapter 4 includes the development of the first iron-catalyzed cross-coupling reaction in the Fu lab-the reductive cross-coupling reaction of readily available olefins with unactivated 1° alkyl electrophiles, including the discovery of the surprising effect of a magnesium salt, substrate scope, and preliminary mechanistic study. Additionally, at the end of this chapter, efforts towards the optimization of an iron-catalyzed reductive cross-coupling reaction of olefins with 2° alkyl electrophiles are reported. The effects of ligands are examined in detail.Chapter 5 outlines the discovery and optimization of a novel copper-catalyzed asymmetric alkylation reaction of a variety of nucleophiles.
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