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YLIJOKI RESEARCH GROUP
Research at the interface of several disciplines
YLIJOKI RESEARCH GROUP
Dr. Kai E. O. Ylijoki
Assistant Professor
Saint Mary's University
Welcome to the website of the Ylijoki Research Group. Our research lies at the interface between organometallic chemistry, organic chemistry, and computational chemistry.
BIOGRAPHY
Dr. Ylijoki began his academic career at Lakehead University in Thunder Bay, ON, where he obtained his Honour's BSc. and MSc. degrees, both under the supervision of Dr. Christine Gottardo. From there, he went to the University of Alberta for his Ph.D. in the group of Dr. Jeffrey M. Stryker. Postdoctoral studies in the group of Dr. E. Peter Kündig of the University of Geneva followed. After returning to Canada, a brief postdoctoral stint at the Biorefining Research Institute at Lakehead University was undertaken in the group of Dr. Robert Dekker before accepting a position as assistant professor at Saint Mary's University in Halifax, NS.
PUBLICATIONS
Journal Articles
16. Land, M. A.; Huo, B.; Robertson, K. N.; Ylijoki, K. E. O.; Lee, P. T. K.; Areephong, J.; Vidovíc, D.; Clyburne, J. A. C. “Coordination Reactivity, and Structural Properties of Electron-Rich Ethoxy- and Dimethylamino-Substituted 1,3-Diketiminates and their Complexes” Dalton Trans. 2018, 47, 10195-10205.
15. Mbaezue, I. I.; Ylijoki, K. E. O. “[5 + 1 + 2 + 1] vs. [5 + 1 + 1 + 2] Rhodium-Catalyzed Cycloaddition Reactions of Vinylcyclopropanes with Terminal Alkynes and Carbon Monoxide: Density Functional Theory Investigations of Competing Mechanistic Pathways and Reaction Regioselectivity” Organometallics 2017, 36, 2832-2842.
14. Publicover, E. A.; Kolwich, J.; Stack, D. L.; Doué, A. J.; Ylijoki, K. E. O. “Crystal Structure of (S)-sec-butylammonium (L)-tartrate monohydrate” Acta Cryst. 2017, E73, 716-719.
13. Ramful, C. D.; Konway, Z. E.; Boudreau, S.; Areephong, J.; Robertson, K. N.; Ylijoki, K. E. O. “Confirmation of the pentadienyl/alkyne [5 + 2] cycloaddition reactivity of the Cp*Co(eta5-1,2,5-trimethylpentadienyl)+ complex” J. Organomet. Chem. 2016, 824, 166-171.
12. Quesnel, J. S.; Moncho, S.; Ylijoki, K. E. O.; Torres, G. M.; Brothers, E. N.; Bengali, A. A.; Arndtsen, B. A. “Computational Study of the Palladium-Catalyzed Carbonylative Synthesis of Aromatic Acid Chlorides: The Synergistic Effect of P(tBu)3 and CO on Reductive Elimination” Chem. Eur. J. 2016, 22, 15107-15118. (Hot Paper)
11. Ramful, C. D.; Robertson, K. N.; Ylijoki, K. E. O. “Crystal Structure of Bis(eta2-ethylene)(eta5- pentamethylcyclopentadienyl)cobalt” Acta Cryst. 2016, E72, 1301-1304. (September 2016 Acta Crystallographica Section E Cover Illustration)
10. Areephong, J.; Huo, B.; Mbaezue, I. I.; Ylijoki, K. E. O. “Synthesis of dihydroquinoxaline-2(1H)-ones via palladium-catalyzed intramolecular C-N bond formation” Tetrahedron Lett. 2016, 57, 3124-3126.
9. Ylijoki, K. E. O.; Kirk, A. D.; Böcklein, S.; Witherell, R. D.; Stryker, J. M. “Cobalt-Mediated eta5-Pentadienyl/Alkyne [5+2] Cycloaddition Reactions: Substitution Effects, Bicyclic Synthesis, and Photochemical h4-Cycloheptadiene Demetallation” Organometallics 2015, 34, 3335-3357.
8. Leigh, F.; Ylijoki, K. E. O.; Garcia, M. T.; Singer, R. D.; Scammells, P. J. Nitrogen Containing Ionic Liquids: Biodegradation Studies and Utility in Base-Mediated Reactions” Aust. J. Chem. 2015, 68, 849-857.
7. Ylijoki, K. E. O.; Stryker, J. M. “[5+2] Cycloaddition Reactions in Organic and Natural Product Synthesis” Chem. Rev. 2013, 113, 2244-2266.
6. Dey, C.; Katayev, D.; Ylijoki, K. E. O.; Kündig, E. P. “Aza-Oxindole Synthesis via Base Promoted Truce-Smiles Rearrangement” Chem. Commun. 2012, 48, 10957-10959.
5. Ylijoki, K. E. O.; Lavy, S.; Fretzen, A.; Kündig, E. P.; Berclaz, T.; Bernardinelli, G.; Besnard, C. “A Synthetic and Mechanistic Investigation of the Chromium Tricarbonyl-Mediated Masamune-Bergman Cyclization. Direct Observation of a Ground State Triplet p-Benzyne Biradical” Organometallics 2012, 31, 5396-5404.
4. Ylijoki, K. E. O.; Budzelaar, P. H. M.; Stryker, J. M. “A Density Functional Theory Investigation of the Cobalt-Mediated eta5-Pentadienyl/Alkyne [5+2] Cycloaddition Reaction: Mechanistic Insight and Substituent Effects” Chem. Eur. J. 2012, 18, 9894-9900.
3. Ylijoki, K. E. O.; Kündig, E. P. “The Preparation of 2H-1,4-Benzoxazin-3-(4H)-ones via Palladium-Catalyzed Intramolecular C-O Bond Formation” Chem. Commun. 2011, 47, 10608-10610.
2. Ylijoki, K. E. O.; Witherell, R. D.; Kirk, A. D.; Böcklein, S.; Lofstrand, V. A.; McDonald, R.; Ferguson, M. J.; Stryker, J. M. “Synthesis, Structure, and Reactivity of Alkyl-Substituted Half-Sandwich eta5-Pentadienyl Complexes of Cobalt” Organometallics 2009, 28, 6807-6822.
1. Witherell, R. D.; Ylijoki, K. E. O.; Stryker, J. M. “Cobalt-Mediated eta5-Pentadienyl/Alkyne [5+2] Cycloaddition. Synthesis and Characterization of Unbridged eta2,eta3-Coordinated Cycloheptadienyl Complexes” J. Am. Chem. Soc. 2008, 130, 2176-2177.
RESEARCH INTERESTS
Our research currently is focused on the development of new catalytic systems for cobalt and rhodium, design of new ligand classes to support catalytic and stoichiometric synthesis, and combined computational/spectroscopic investigations of metal-catalyzed reaction mechanisms.
TEACHING
Prof. Ylijoki currently teaches courses and labs at the 1st, 2nd, and 4th year levels. Course descriptions are provided below.
Previously, CHEM 1212 – General Chemistry II for Life Sciences and CHEM 2345 – Organic Chemistry II have been offered, along with directed studies courses at the graduate level.
CHEM 2344 – ORGANIC CHEMISTRY I
September - December, 2017
An introduction to organic chemistry designed for all students in life science, physical science, general science, engineering or non-science. Topics covered include the structure, nomenclature, physical properties, synthesis, reactions and spectroscopic properties of all classes of hydrocarbons: alkanes, alkenes, alkynes, arenes, alicyclic compounds, polyenes, as well as the principle heterocyclic compounds. The course emphasizes the mechanistic approach to the reactivity of organic compounds and provides a thorough introduction to stereochemistry and nuclear magnetic resonance.
CHEM 4499 – SELECTED RESEARCH TOPICS IN CHEMISTRY
September - December, 2017
A weekly seminar course that covers a broad range of research topics that are of current relevance, including ethics in science. Speakers include faculty from within and outside Saint Mary's University and students will normally be expected to present two seminars.
CHEM 1211 – GENERAL CHEMISTRY II FOR PHYSICAL SCIENCE
January - April, 2018
A continuation of the introduction to general topics in chemistry including chemical equilibrium and applications to aqueous systems, physical equilibrium, thermodynamics, reaction kinetics, molecular structure, electrochemistry and organic chemistry. Emphasis is placed on applications to the physical sciences, including chemistry, geology and physics.
CHEM 4444 – SYNTHESIS IN ORGANIC CHEMISTRY
January - April, 2018
Of study of the principles involved in the planning and execution of the synthesis of organic molecules. The focus of the course is on studying published total syntheses to better understand how complex molecule synthesis is planned and executed.