Laina M. Geary

Assistant Professor
Laina Geary

Contact Information

Degrees

  • Banting NSERC Postdoctoral Fellow (2010-2014), University of Texas at Austin (M. J. Krische)
  • Ph.D. (2010), University of Manitoba (P. G. Hultin)
  • B.Sc. Hons. (2005), University of Manitoba

Research Interests

Research in the Geary laboratory focuses on the development and application of transition metal chemistry in catalysis and synthetic chemistry to the formation of carbon-carbon bonds. The research is divided into three general themes.

The first focuses on the catalytic generation of reactive intermediates. By avoiding stoichiometric, preformation of highly reactive intermediates, we aim to direct the reactivity of these species in a controlled and selective manner. A second area of focus is on rendering traditional, stoichiometric organic reactions into catalytic processes. A third area of focus is the invention of new catalytic reactions for the construction of carbon-carbon bonds. These are not mutually exclusive concepts, and the interplay between two or more areas drives the research program. The study of reaction mechanism is central to all projects and leads to both a deeper understanding of chemical processes and to the discovery of new chemistry.

One key concept in the design of projects involves the availability of the starting materials. The degrees of separation between the commodity or feedstock chemical and the starting material for the C-C bond forming reaction should be kept to a minimum, and are ideally zero. This necessitates the conceptualization of targets and goals from the very beginning, and provides a focus for the idealization of chemistries developed. The terms atom economy, step economy, and redox economy frequently appear in the literature, and serve to emphasize the importance of chemoselectivity in any transformation. High chemoselectivity is a standing goal to maximize the functional group compatibility and minimize substrate preactivation. Students receive training in organic synthesis, organometallic chemistry, and asymmetric catalysis within the broad goal of simplicity to complexity via C-C bond formation.

interplay

Publications

  • Ricker, J.D.; Mohammadrezaei, V.; Crippen, T.J.; Zell, A.M.; Geary, L.M.  Nitrous Oxide Promoted Pauson-​Khand Cycloadditions.  Organometallics 2018, 37, 4556-4559.
  • Ricker, J.D.; Geary, L.M.  Recent Advances in the Pauson-Khand Reaction.  Top. Catal. 2017, 60, 609.
  • Li, L.; Stimac, J.C.; Geary, L.M.  Synthesis of olefins via a Wittig reaction mediated by triphenylarsine.  Tetrahedron Lett. 2017, 58, 1379.
  • Perez, F.; Oda, S.; Geary, L.M.; Krische, M.J.  Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation:  Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.  Top. Curr. Chem. 2016, 374, 1.
  • Kasun, Z.A.; Geary, L.M.; Krische, M.J.  Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenation [4+2]-cycloaddition.  Chem. Commun. (Cambridge, U. K.) 2014, 50, 7545.
  • Geary, L.M.; Chen, T.-Y.; Montgomery, T.P.; Krische, M.J.  Benzannulation via Ruthenium-Catalyzed Diol-Diene [4+2] Cycloaddition:  One- and Two-Directional Syntheses of Fluoranthenes and Acenes.  J. Am. Chem. Soc. 2014, 136, 5920.
  • Geary, L.M.; Glasspoole, B.W.; Kim, M.M.; Krische, M.J.  Successive C-C Coupling of Dienes to Vicinally Dioxygenated Hydrocarbons:  Ruthenium Catalyzed [4+2] Cycloaddition across the Diol, Hydroxycarbonyl or Dione Oxidation Levels.  J. Am. Chem. Soc. 2013, 135, 3796.
  • Geary, L.M.; Leung, J.C.; Krische, M.J.  Ruthenium Catalyzed Reductive Coupling of 1,3-Enynes and Aldehydes via Transfer Hydrogenation:  anti-Diastereoselective Carbonyl Propargylation.  Chem.-Eur. J. 2012, 18, 16823.
  • Leung, J.C.; Geary, L.M.; Chen, T.-Y.; Zbieg, J.R.; Krische, M.J.  Direct, Redox-Neutral Prenylation and Geranylation of Secondary Carbinol C-H Bonds:  C4-Regioselectivity in Ruthenium-Catalyzed C-C Couplings of Dienes to alpha-Hydroxy Esters.  J. Am. Chem. Soc. 2012, 134, 15700.
  • Woo, S.K.; Geary, L.M.; Krische, M.J.  Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chloride.  Angew. Chem., Int. Ed. 2012, 51, 7830.
  • Geary, L.M.; Woo, S.K.; Leung, J.C.; Krische, M.J.  Diastereo- and Enantioselective Iridium-Catalyzed Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level:  1,3-Enynes as Allenylmetal Equivalents.  Angew. Chem., Int. Ed. 2012, 51, 2972.