The Fall 2022 GWC2 Seminar Series continues Wednesday, November 16th with two pesentations by PhD candidates from the University of Guelph.
Experimental and Theoretical Investigations of Iridium-Catalyzed Reactions Involving Heterobicyclic Alkenes
Austin
Pounder,
PhD
candidate
Department
of
Chemistry
University
of
Guelph
Abstract
for
Austin
Pounder's
seminar
And
Modular Approaches for the Generation of Fluorescent Nucleobase Surrogates and their use in Biosensing Applications
Ryan
Johnson,
PhD
candidate
Department
of
Chemistry
University
of
Guelph
Abstract
for
Ryan
Johnson's
seminar
Wednesday,
November
16,
2022
3:00
p.m.
MacN
101
at
the
University
of
Guelph
-
Coffee
and
snacks
served.
Online
via
Microsoft
Teams
for
the
University
of
Waterloo.
Please
contact
gwc@uoguelph.ca
with
your
Teams
ID/email
address
to
attend
the
seminars
online.
All
are
welcome
to
attend!
Experimental and Theoretical Investigations of Iridium-Catalyzed Reactions Involving Heterobicyclic Alkenes
Austin Pounder, PhD candidate, Department of Chemistry, University of Guelph
ABSTRACT: Over the last 20 years, transition metal-catalyzed transformations of heterobicyclic alkenes have been an intense area of research. Although this methodology has proven valuable for the synthesis of stereodefinedcyclic and acyclic synthetic building blocks, it is primarily governed by the interconversion of pre-existing functional groups. While these traditional cross-coupling reactions have revolutionized the modern chemist’s synthetic toolbox, prior installation of these functional groups requires a number ofsteps, leading to undesired side-products and reduced overall yield. An attractive solution to this problem is the catalytic activation and subsequent functionalization of otherwise inert carbon−hydrogen bonds. In this seminar, I will present the experimental and theoretical investigations of two iridium-catalyzed reactions involving heterobicyclic alkenes. First, an iridium/zinc co-catalyzed ring-opening reaction of heterobicyclic alkenes with C3-selective indole nucleophiles. Secondly, an iridium-catalyzed hydroacylation reactions of unsymmetrical oxabicyclic alkenes with salicylaldehyde. Through experimentation and quantum modeling, we attempt to reveal the mechanistic underpinnings and origins of chemo-, regio-and stereoselectivity observed in these 100% atom economic reactions.
Modular Approaches for the Generation of Fluorescent Nucleobase Surrogates and their use in Biosensing Applications
Ryan Johnson, PhD candidate, Department of Chemistry, University of Guelph
ABSTRACT: Nucleic acids have become a functional and easily accessible material, due to their practical synthesis enabled by solid phase phosphoramiditechemistry. As such, over the last 20-30 years, there has been a large growth in research areas devoted to studying how nucleic acids interact and behave with one another and various biopolymers. Fluorescent probes represent a critical tool for this area of research, as they can bind nucleic acids and respond to changes in the microenvironment. Typically, free fluorescent labels are employed, as they are commercially available or easily accessible through known building blocks. Unfortunately, free fluorescent labels can bind non-specifically, and offer no site-specific information. A solution to this problem involves the use of internal fluorescent labels, although this method generally involves complicated syntheses which hampers their broadened use. Thus, it is desirable to create internal fluorescent probes which are user friendly and lack complicated synthesis, yet still retain high functionality. In this seminar, three easily accessible and modular “building-blocks” will be presented, which when further functionalized, create three unique libraries of fluorescent probes. Biosensing applications of the respective libraries will also be presented, with examples including heavy metal detection, protein detection, and observation of DNA hybridization.