Laina M. Geary

Associate Professor She/her/hers

Summary

Laina was born and raised in Winnipeg, Manitoba, Canada. She completed her B.Sc.(Hons.) in 2005 at the University of Manitoba with first class honours. She stayed at the U of M to pursue a Ph.D. under the guidance of Prof. Philip Hultin. As an NSERC postgraduate scholar, she studied the behavior of trichloroethylene derivatives under palladium-catalyzed cross-coupling conditions and developed new routes to benzofurans and indoles via Pd-catalyzed C-H functionalization and earned a Ph.D. in 2010. She then joined the research lab of Prof. Michael Krische at the University of Texas at Austin where she studied ruthenium(II)- and iridium(I) catalyzed propargylation reactions. In 2011, Laina became one of the inaugural recipients of a Banting Postdoctoral Fellowship through NSERC. Laina's last projects at UT involved the discovery and development of two new patterns of reactivity of ruthenium(0) catalysts. Laina joined the University of Nevada, Reno in July 2014 as an assistant professor.

research interests

Our research group has two broad objectives: to develop robust and chemoselective catalytic methods for C-C and C-X bond formation, and to understand the mechanisms by which they proceed. We use both transition metal and Lewis acid catalysis to enable bond formation, and collaborate with spectroscopists to study organometallic intermediates. Some of our current research projects are outlined below.

Pauson-Khand Reaction

The Pauson-Khand reaction is a [2+2+1] cycloaddition that couples an alkyne, alkene and carbon monoxide to generate 3 new C-C bonds and furnish a cyclopentenone. Our interests in the PKR are both synthetic and mechanistic.

Though known for more than 40 years, there are a number of synthetic limitations. Insertion of the alkyne component is completely selective for the substituent to incorporate at the alpha position; if a disubstituted alkyne is used, mixtures usually ensue. We have identified simple, inexpensive alkynes to address that. We are also developing new chemistry that will allow the incorporation of alpha-olefins in an intermolecular PKR for the first time! Typical PKR chemistry is mediated by N-oxides, and we are developing alternates to the currently used oxides, as well alternates to CO gas.

Our collaboration with the Shearer group (Trinity University) is on the characterization of the organocobalt intermediates, and we're also developing chemistry that avoids typical norbornenes in the reaction.

Catalytic Olefination

The Wittig reaction was discovered over 60 years ago, yet remains one of the most common methods to synthesized C=C double bonds on small scales. However, the stoichiometric generation of phosphine oxide waste has greatly limited the application of the Wittig reaction on more substantial scales.

We are interested in developing a catalytic method that uses a simple oxygen sink to enable the C=C bond formation. Some of our preliminary data related to a stoichiometric method were published recently, and our first paper on a catalytic variant should be in print not too long from now!

N-Oxides in Synthesis

Our recent work with nitrous oxide in Pauson-Khand chemistry has led us to explore nitrous oxide in other reactions, as well as the application and study of other N-oxides in synthesis.

Direct Substitution of Alcohols

We are also interested in the selective construction of C-C and C-X bonds via the direct substitution of alcohols. The preliminary results on this should be published shortly, and it has led to some new chemistry related to Piancatelli reactivity (carbocationic intermediates). This has unveiled some interesting mechanistic observations!

Education

  • BSc(Hons), Chemistry, University of Manitoba (2005)
  • PhD, Organic Chemistry, University of Manitoba (2010)

Please visit Dr. Geary's Google Scholar profile to view a complete list of publications

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