The Investigation of Novel Nickel Catalysts and Their Application to Organic Synthesis

Jeremy Duczynski

doi:10.26182/ar6h-h514

The Investigation of Novel Nickel Catalysts and Their Application to Organic Synthesis

Jeremy Duczynski

School of Molecular Sciences

Research output: Thesis › Doctoral Thesis

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Abstract

This thesis describes the development of new nickel(0) and nickel(II) complexes containing both N-heterocyclic carbene and phosphite ligands. New three-coordinate nickel(0) complexes were shown to be highly capable catalysts for the Suzuki-Miyaura cross-coupling of aryl tosylates with boronic acids. Mechanistic details of this reaction were elucidated by the isolation and characterisation of a reaction intermediate as well as through NMR studies. Also explored in the thesis is the application of tert-butyldimethylsilyl amine as an effective silylating agent for phenols, benzyl alcohols and carboxylic acids under mild and solvent-free conditions.

Original language	English
Qualification	Doctor of Philosophy
Awarding Institution	The University of Western Australia
Supervisors/Advisors	Stewart, Scott, Supervisor Dorta, Reto, Supervisor Fuller, Becky, Supervisor
Thesis sponsors	Australian Government Research Training Program
Award date	22 Feb 2021
DOIs	https://doi.org/10.26182/ar6h-h514
Publication status	Unpublished - 2021

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10.26182/ar6h-h514

THESIS - DOCTOR OF PHILOSOPHY - DUCZYNSKI, Jeremy Andrew - 2021
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Cite this

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title = "The Investigation of Novel Nickel Catalysts and Their Application to Organic Synthesis",

abstract = "This thesis describes the development of new nickel(0) and nickel(II) complexes containing both N-heterocyclic carbene and phosphite ligands. New three-coordinate nickel(0) complexes were shown to be highly capable catalysts for the Suzuki-Miyaura cross-coupling of aryl tosylates with boronic acids. Mechanistic details of this reaction were elucidated by the isolation and characterisation of a reaction intermediate as well as through NMR studies. Also explored in the thesis is the application of tert-butyldimethylsilyl amine as an effective silylating agent for phenols, benzyl alcohols and carboxylic acids under mild and solvent-free conditions.",

keywords = "catalysts, catalysis, nickel, silylation, cross-coupling, Suzuki-Miyaura, N-heterocyclic carbene, Phosphite",

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year = "2021",

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language = "English",

school = "The University of Western Australia",

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AU - Duczynski, Jeremy

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Y1 - 2021

N2 - This thesis describes the development of new nickel(0) and nickel(II) complexes containing both N-heterocyclic carbene and phosphite ligands. New three-coordinate nickel(0) complexes were shown to be highly capable catalysts for the Suzuki-Miyaura cross-coupling of aryl tosylates with boronic acids. Mechanistic details of this reaction were elucidated by the isolation and characterisation of a reaction intermediate as well as through NMR studies. Also explored in the thesis is the application of tert-butyldimethylsilyl amine as an effective silylating agent for phenols, benzyl alcohols and carboxylic acids under mild and solvent-free conditions.

AB - This thesis describes the development of new nickel(0) and nickel(II) complexes containing both N-heterocyclic carbene and phosphite ligands. New three-coordinate nickel(0) complexes were shown to be highly capable catalysts for the Suzuki-Miyaura cross-coupling of aryl tosylates with boronic acids. Mechanistic details of this reaction were elucidated by the isolation and characterisation of a reaction intermediate as well as through NMR studies. Also explored in the thesis is the application of tert-butyldimethylsilyl amine as an effective silylating agent for phenols, benzyl alcohols and carboxylic acids under mild and solvent-free conditions.

KW - catalysts

KW - catalysis

KW - nickel

KW - silylation

KW - cross-coupling

KW - Suzuki-Miyaura

KW - N-heterocyclic carbene

KW - Phosphite

U2 - 10.26182/ar6h-h514

DO - 10.26182/ar6h-h514

M3 - Doctoral Thesis

ER -

The Investigation of Novel Nickel Catalysts and Their Application to Organic Synthesis

Abstract

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