Dr. Chae S. Yi

Dr. Chae S. YiMarquette University

Wehr Chemistry Building, 619

MilwaukeeWI53201United States of America(414) 288-3536chae.yi@marquette.eduThe Yi Lab

Professor

Organometallic Chemistry and Homogeneous Catalysis

Education

Ph.D., University of Wisconsin-Madison

B.S., University Michigan-Ann Arbor

Research Interests

Catalytic C-H Bond Activation and Functionalization Reactions

Transition metal catalyzed C-H bond activation reaction is a powerful synthetic method for forming functionalized products directly from unreactive hydrocarbons, and has enormous synthetic potentials for developing chemical processes ranging from petroleum products to pharmaceutical agents. Catalytic C-H bond activation method also has high potential for “reforming” fossil fuels and biomass for obtaining clean and environmentally sustainable chemical energy. One of the long term goals of our group’s research to design effective metal catalysts, which can facilitate efficient and selective C-H bond activation reactions of synthetic importance. This research group recently discovered a number of highly effective coupling reactions involving C-H bond activation (see below reaction scheme) by using well-defined ruthenium catalysts. We are currently investigating the detailed reaction mechanisms of these catalytic reactions, and are searching for novel C-H coupling reactions of synthetic importance by using well-defined ruthenium catalysts.

Cooperative Ruthenium Catalysts for Unreactive Bond Activation Reactions

Another major area of our group’s research centers on the synthetic and mechanistic study of the cooperative reactivity of multinuclear ruthenium catalysts for synthetically useful chemical transformations. Cooperative catalysis by multinuclear transition metal complexes has long been regarded as an effective way to control and regulate chemical reactions that are normally difficult to achieve from monometallic ones, and can serve as functional models for natural allosteric metalloenzymes. Multinuclear ruthenium cluster complexes have long been considered as functional models for promoting cooperative activity for unreactive C-H, C-C and C-N bond activation reactions. We recently discovered that the bi- and tetrametallic ruthenium-hydroxo complexes are highly cooperative catalysts for the alcohol oxidation and nitride hydration reactions, and are studying to attain fundamental mechanistic knowledge on the cooperative nature of the ruthenium-hydroxo catalysts for these reactions. We are also engaged in designing and utilization of new cooperative metal catalysts for other coupling reactions involving C-H bond activation.

Selected examples of the catalytic reactions developed in our research group:

GROUP MEMBERS

The group is composed of three graduate students:

· Krishna Gnyawali

· Aldiyar Shakenov

· Dulanjali Thennakoon

Professional Experience

Professor Yi received his B.S. degree from the University Michigan-Ann Arbor in 1987 and Ph.D. from the University of Wisconsin-Madison in 1991. After completing a postdoctoral training at the Pennsylvania State University (1992-93). He joined the department in 1993, was promoted to Associate Professor with tenure in 2000 and Professor in 2011. His area of research is inorganic chemistry, and has been teaching undergraduate/graduate courses in that area. His publication record includes over 46 publications in inorganic chemistry, most of them in American Chemical Society journals. He recently received an NSF grant studying catalytic C-H bond activation reactions. This work will develop new "green" catalytic processes that will give desired products efficiently without forming wasteful byproducts under environmentally compatible conditions.

Selected Publications

Please see the full list on Google Scholar.

1. Scope and Mechanistic Analysis for Chemoselective Hydrogenolysis of Carbonyl Compounds Catalyzed by a Cationic Ruthenium-Hydride Complex with Tunable Phenol Ligand. Kalutharage, N.; Yi, C. S. J. Am. Chem. Soc. 2015, 137, 11105-11114.
2. Catalytic Tandem Dehydrogenation-Alkylation and -Insertion Reactions of Saturated Hydrocarbons with Alcohols and Alkenes. Kim, J.; Pannilawithana, N.; Yi, C. S. ACS Catal. 2016, 6, 8395-8398.
3. Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand Promoted Ruthenium Catalyzed Deaminative Coupling Reaction of Primary Amines. Arachchige, P. T. K.; Lee, H.; Yi, C. S. J. Org. Chem. 2018, 83, 4932-4947.
4. Experimental and Computational Study of the (Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones. Lee, H.; Mane, M. V.; Ruy, H.; Sahu, D.; Baik, M.-H.; Yi, C. S. J. Am. Chem. Soc. 2018, 140, 10289-10296.
5. Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand Promoted Ruthenium Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines. Arachchige, P. T. K.; Yi, C. S. Org. Lett. 2019, 21, 3337-3341.
6. Catalytic Carbon–Carbon Bond Activation of Saturated and Unsaturated Carbonyl Compounds via Chelate-Assisted Coupling Reaction with Indoles. Pannilawithana, N.; Yi, C. S. ACS Catal. 2020, 10, 5852-5861.
7. Experimental and Computational Studies on the Ruthenium-Catalyzed Dehydrative C–H Coupling of Phenols with Aldehydes for the Synthesis of 2-Alkylphenol, Benzofuran and Xanthene Derivatives. Pannilawithana, N.; Pudasaini, B.; Baik, M.-H.; Yi, C. S. J. Am. Chem. Soc. 2021, 143, 13428-13440.
8. Scope and Mechanism of the Redox-Active 1,2-Benzoquinone Enabled Ruthenium-Catalyzed Deaminative a-Alkylation of Ketones with Amines. Arachchige, P. T. K.; Handunneththige, S.; Talipov, M. R.; Kalutharage, N.; Yi, C. S. ACS Catal. 2021, 11, 13962-13972.
9. Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2’-Hydroxyarylketones and 2-Aminobenzamides with Simple Amines. Gnyawali, K.; Arachchige, P. T. K.; Yi, C. S. Org. Lett. 2022, 24, 218.