Development of Site-Selective C-H Functionalization Strategies for Azaheterocycles

Kaur, Milanpreet

Development of Site-Selective C-H Functionalization Strategies for Azaheterocycles

dc.contributor.advisor	Van Humbeck, Jeffrey Francis
dc.contributor.author	Kaur, Milanpreet
dc.contributor.committeemember	Derksen, Darren Jason
dc.contributor.committeemember	Sutherland, Todd C.
dc.contributor.committeemember	Shimizu, George Kisa Hayashi
dc.contributor.committeemember	Watson, Allan J. B.
dc.date	2024-11
dc.date.accessioned	2024-08-01T15:51:03Z
dc.date.available	2024-08-01T15:51:03Z
dc.date.issued	2024-07-26
dc.description.abstract	C-H activation is an area of major ongoing research exploration and has emerged as a valuable addition to the organic chemist’s toolbox for the rapid construction of compounds that are of great interest to the pharmaceutical industry. More specifically, recent work has focused on C-H activation at a late stage in complex and biologically relevant molecules. Recently, activation of C-H bonds in heterocycles has emerged as a new route in the synthesis of heterocycles. In particular, the transformation of the C-H bond into C-X bond (where= carbon, oxygen or nitrogen) in heterocycles has gained interest due to its availability in biologically active pharmaceuticals, agrochemicals, and natural products. Although various approaches have been developed for activating C-H bonds in azaheterocycles, there has been a noticeable challenge in a) carrying competitive C-H functionalization when several sites of comparable reactivity are present; and b) accessing many possible reactive sites within a substrate. This work showcases the development of a novel site-selective C-H functionalization strategy in azaheterocycles by taking substrates with different C-H bonds of comparable reactivity and selectivity and converting only one of those C-H bonds predictably into a new carbon-element bond. The goal was to do so using catalyst control and without including any directing groups. This research begins with the development of a new site-selective benzylic C-H hydroxylation in electron-deficient azaheterocycles, encompassing a diverse range of substrates. The latter part of the thesis addresses the challenges associated with the site-selective amination strategy previously developed by our group. In-depth research was conducted to develop catalytic systems capable of selectively and predictably aminating the C-H bond adjacent to an azaheterocycle. Additionally, extensive research was conducted towards synthesizing and deprotecting aminating reagents as well as utilizing photochemistry to install a selective hydrazine/amine unit that can be used to direct other C-H functionalization chemistries.
dc.identifier.citation	Kaur, M. (2024). Development of site-selective C-H functionalization strategies for azaheterocycles (Doctoral thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca.
dc.identifier.uri	https://hdl.handle.net/1880/119303
dc.language.iso	en
dc.publisher.faculty	Graduate Studies
dc.publisher.institution	University of Calgary
dc.rights	University of Calgary graduate students retain copyright ownership and moral rights for their thesis. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.
dc.subject	Heterocycles
dc.subject	Site-Selective Reaction
dc.subject	Amination
dc.subject	Hydroxylation
dc.subject	C-H Functionalization
dc.subject.classification	Chemistry--Organic
dc.title	Development of Site-Selective C-H Functionalization Strategies for Azaheterocycles
dc.type	doctoral thesis
thesis.degree.discipline	Chemistry
thesis.degree.grantor	University of Calgary
thesis.degree.name	Doctor of Philosophy (PhD)
ucalgary.thesis.accesssetbystudent	I do not require a thesis withhold – my thesis will have open access and can be viewed and downloaded publicly as soon as possible.