Department of Chemistry

Catalytic C-H bond activation is a highly attractive strategy in green and sustainable covalent synthesis for drugs, natural products and advances materials from simple organic hydrocarbons. Our program systematically established a revolutionary approach in exploiting synergistic effect between main and transition metal to promote efficient selective C-H activation. The following highlights are our several breakthrough discoveries, which led to several significant contributions in the field of chemical science and catalysis, particularly on the development and the understanding of bimetallic cooperative effect on CH activation. (Total citation more than 200 times with several 11 top prestigious 5% scientific publications. Our other research endeavor is also focused on developing and design novel scaffold of ligand framework with the aim of pushing the boundaries of current concept and chemical knowledge. Some of our current interests include (a) functional linked nitrogen-heterocyclic carbene (NHC) and (b) carbodicarbenes, which were used to isolate uniquely chemical structures and to discover interestingly reactivities in transition metals and main group elements. Evidently, our works in CH activation, main group chemistry and ligand design have been recognized with numerous international and national awards as listed below here:

• 2010 Outstanding Young Investigator award (The Taiwan Chemical Society).


• 2012 The Outstanding Young Researcher Grant Award (National Science Council).


• 2013 Distinguished Lectureship Award in Asian (The Chemical Society of Japan)


• 2014 Award for Outstanding Young Scholar, Shui-Mu Foundation of Chemistry (Taiwan).

Research Fellow (2015-)；Associate Research Fellow (2011-2015)；Assistant Research Fellow (2006-2011)；B.S., WinonaStateUniversity, Winona, Minnesota, U.S.A. (1994)；Ph.D., University of Kentucky, Lexington, Kentucky, U.S.A. (2000)；Postdoctoral Scientist, University of California at Santa Barbara, California, U.S.A. (2000-2001)；Postdoctoral Researcher and Lecturer, University of Ottawa, Ontario, Canada. (2004-2005)；

Young Chemists Award of the Chemical Society Located in Taipei(2010)； Distinguished Lectureship Award from The Chemical Society of Japan Asian International Symposium(2013)；Award for Outstanding Young Scholar, Shui-Mu Foundation of Chemistry(2014)；

1. Hsu, Y.-C.; Shen, J.-S.; Lin, B.-C.; Chen, W.-C.; Chan, Y.-T.; Ching, W.-M.; Yap, G. P. A.; Hsu, C.-P.; Ong, T.-G. Isolation of Tridentate Acyclic Bis(Pyridine)carbodicarbene and Further Studies on Its Structural Implications and Reactivities. Angew. Chem. Int. Ed. 2014, Accepted for publication.


2. Yu, M.-S.; Lee, W.-C.; Chen, C.-H.; Tsai, F.-Y.; Ong, T.-G. Controlled Regiodivergent C-H Bond Activation of Imidazo[1,5-a]pyridine via Synergistic Cooperation between Aluminum and Nickel. Organic Letters, 2014, Accepted for publication. .


3. Chen, W.-C.; Lai, Y.-C.; Shih, W.-C.; Yu, M.-S.; Yap, G. P. A.; Ong, T.-G. Mechanistic Study of the Regioselective Switch for Hydroheteroarylation of Styrene Catalyzed by Bimetallic Ni-Al via C-H Activation. Chem.-Eur. J. 2014, 20, 8099.


4. Huang, H.-J.; Lee, W.-C.; Yap, G. P. A.; Ong, T.-G. Synthesis and Characterization of Amino-NHC Coinage Metal Complexes and Application for C-H Activation of Caffeine. J. Organomet. Chem. 2014, 761, 64.


5. Tai, C.-C; Yu, M.-S.; Chen, Y.-L.; Chuang, W.-H.; Lin T.-H.; Yap, G. P. A.; Ong, T.-G. Synthesis of a Guanidine NHC complex and its Application in Borylation Reactions. Chem. Commun. 2014, 50, 4344.


6. Lee, W.-C.; Wang, T.-H.; Ong, T.-G. Ligand promoted Pd-catalyzed dehydrogenative alkenylation of hetereoarenes. Chem. Commun. 2014, 50, 3671.


7. Chen, C.-C.; Lee, C.-Y.; Lin, B.-C.; Hsu, Y.-C.; Shen, J.-S.; Hsu, C.-P.; Yap, G. P. A.; Ong, T.-G. The Elusive Three-Coordinate Dicationic Hydrido Boron Complex. J. Am. Chem. Soc. 2014, 136, 914.


8. Lee, W.-C.; Wang, C.-H.; Lin Y.-H.; Shih, W.-C.; Ong, T.-G. Tandem Isomerization and C–H Activation: Regioselective Hydroheteroarylation of Allylarenes. Organic Letters, 2013, 15, 5358.


9. Chen, C. T.; Chen, C. H.; Ong, T.-G. Complementary Helicity Interchange of Optically Switchable Supramolecular-Enantiomeric Helicenes with (−)-Gel-Sol-(+)-Gel Transition Ternary Logic. J. Am. Chem. Soc 2013, 135, 5294.


10. Chen, W. C.; Hsu, Y. C.; Lee, C. Y.; Yap, G. P. A.; Ong, T.-G. Synthetic Modification of Acyclic Bent Allenes (Carbodicarbenes) and Further Studies on Their Structural Implications and Reactivities. Organometallics, 2013, 32,2435.


11. Titel, J.; Chen, W. C.; Michel, S.; Korobkov, I.; Ong, T.-G. Richeson, D. S. Solid-State Thermolysis of a fac-Rhenium(I) Carbonyl Complex with a Redox Non-Innocent Pincer Ligand. Chem.-Eur. J. 2013, 19, 4278.


12. Chen, W. C.; Hsu, Y. C.; Shih, W. C.; Lee, C. Y.; Chuang, W. H.; Tsai, Y. F.; Chen, P. P. Y.; Ong, T.-G. Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes. Chem. Commun. 2012, 48, 6702.


13. Liu, Y. M.; Lin, Y. C.; Chen, W. C.; Cheng, J. H.; Yap, G. P. A. Sun S. S; Ong, T.-G. Synthesis and Characterization of a para-Pyridine Linked NHC Palladium Complexes and their Studies for Heck-Mizoroki Coupling Reaction. Dalton Transactions, 2012, 41, 7382.


14. Shih, W. C.; Chen, W. C.; Lai, Y. C.; Yu, M. Y.; Ho, J. J.; Yap, G. P. A.; Ong, T.-G. The Regioselective Switch for Amino-NHC Mediated C-H Activation of Benzimidazole via Ni-Al Synergistically Catalysis. Organic Letters, 2012, 14, 2046.


15. Tai, C. –C.; Chang, Y. –T.; Tsai, J. –H.; Jurca, T.; Yap, G. P. A.; Ong, T. –G. Subtle Reactivities of Boron and Aluminum Complexes with Amino-Linked N-Heterocyclic Carbene Ligation. Organometallics, 2012, 31, 637.


16. Wang, C.-H; Shih, W.-C.; Chang, H.-C.; Kuo, E.; Hung, W.-C.; Ong, T.-G.; Li, W.-S. Preparation and Characterization of Amino-Linked Heterocyclic Carbene Palladium, Gold, and Silver Complexes: Applications in Anticancer Agents via Triggering Apoptotic Cell Death. J. Med. Chem. 2011, 54, 5245.


17. Li, C.-Y.; Kuo, Y.-Y; Tsai, J.-H.; Yap, G. P. A.; Ong, T.-G. Amine-Linked N-Heterocyclic Carbene: The importance of an Pendant Free Amine Auxiliary in Assisting the Catalytic Reaction. Chem. Asian J. 2011, 6, 1520.


18. Tsai, J.-H.; Lin, S.-T.; Yang, R. B.G.; Yap, G. P. A.; Ong, T.-G. The Two-way Street Transformation of Boronium and Borane Complexes Facilitated by Amino-Linked N-Heterocyclic Carbene. Organometallics 2010, 29, 4004.


19. Tsai, C. –C.; Shih, W.-C.; Fang, C.-H.; Li, C.-Y.; Ong, T.-G.; Yap, G. P. A. Bimetallic Nickel Aluminun Mediated Para-Selective Alkenylation of Pyridine: Direct Observation of η2,η1-Pyridine Ni(0)−Al(III) Intermediates Prior to C−H Bond Activation. J. Am. Chem. Soc. 2010, 132, 11887.


20. Hu, Y.-C.; Liang, C.-F.; Tsai, J.-H.; Yap, G. P. A.; Chang, Y.-T.; Ong, T.-G. Zirconium Complexes Supported by Imidazolones: Synthesis, Characterization, and Application of Precatalysts for the Hydroamination of Aminoalkenes. Organometallics 2010, 29, 3357.


21. Hu, Y.-C.; Tsai, C.-C.; Shih, W.-C.; Yap, G. P. A.; Ong, T.-G. The Zirconium Benzyl Mediated C-N Bond Cleavage of an Amino-Linked N-Heterocyclic Carbene. Organometallics 2010, 29, 516.


22. Shih, W. -C.; Wang, C.-H.; Chang, T.-T.; Yap, G. P. A.; Ong, T-G. Synthesis and Structure of an Amino- Linked N-Heterocyclic Carbene and the Reactivity of its Aluminum Adduct. Organometallics 2009, 47, 1060.


23. Huang, Y.-P.; Tsai, C.-C.; Shih, W.-C.; Chang, Y.-C.; Lin, S.-T.; Yap, G. P. A.; Chao, I.; Ong, T-G. Kinetic and Thermodynamic Study of Syn—Anti Isomerization of Nickel Complexes Bearing Amino-Linked N-Heterocyclic Carbene Ligands: The Effect of the Pendant Arm of the NHC. Organometallics 2009, 28, 4316.


24. Rowley, C. N.; Ong, T-G.; Priem, J.; Richeson, D. S.; Woo, T. K. Analysis of the Critical Step in Catalytic Carbodiimide Transformation: Proton Transfer from Amines, Phosphines, and Alkynes to Guanidinates, Phosphaguanidinates, and Propiolamidinates with Li and Al Catalysts. Inorg. Chem. 2008, 47, 12024.


25. Rowley, C. N.; Ong, T-G.; Priem, J.; Woo, T. K.; Richeson, D. S. Amidolithium and Amidoaluminum Catalyzed Synthesis of Substituted Guanidines: An Interplay of DFT Modeling and Experiment. Inorg. Chem. 2008, 47, 9660.


26. Lavoie, N.; Ong, T. G.; Gorelsky, S. I.; Korobkov, I.; Yap, G. P. A.; Richeson, D. S. Bis(imido) W(VI) complexes chelated by N,N '-Disubstituted 1,8-diamidonaphthalene: An analysis of bonding, isocyanate insertion, and Al-Me transfer. Organometallics 2007, 26, 6586.


27. Ong, T. G.; O'Brien, J. S.; Korobkov, I.; Richeson, D. S. Facile and atom-efficient amidolithium-catalyzed C-C and C-N formation for the construction of substituted guanidines and propiolamidines. Organometallics 2006, 25, 4728.


28. Said, F. F.; Ong, T. G.; Bazinet, P.; Yap, G. P. A.; Richeson, D. S. Linking hydrogen dicarboxylate synthons with substituted guanidinium cations: Transforming rings and chains into two- and three-dimensional structures. Cryst. Growth Des. 2006, 6, 1848.


29. Said, F. F.; Bazinet, P.; Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Hydrogen Bonding Motifs of N,N',N' '-Trisubstituted Guanidinium Cations with Spherical and Rodlike Monoanions: Syntheses and Structures of I^-, I₃^-, and SCN- Salts. Cryst. Growth Des. 2006, 6, 258.


30. Said, F. F.; Ong, T.-G.; Yap, G. P. A.; Richeson, D. Strong and Weak Hydrogen-Bonding Interactions in the Structures of N,N',N' '-Trisubstituted Guanidinium Chlorides and Bromides. Cryst. Growth Des. 2005, 5, 1881.


31. Ong, T. G.; Yap, G.; Richeson, D. S. Catalytic C-N bond metathesis of carbodiimides by group 4 and 5 imido complexes supported by guanidinate ligands. Chem. Commun. 2003, 2612.


32. Ong, T. G.; Yap, G.; Richeson, D. S. Catalytic Construction and Deconstruction of Guanidine: Ti-Mediated Guanylation of Amines and Transamination of Guanidines. J. Am. Chem. Soc. 2003, 125, 8100.


33. Ong, T. G.; Yap, G.; Richeson, D. S. Redefining the Coordination Geometry and Reactivity Guanidinate Complexes by Covalently Linking the Guanidine ligands. Organometallics 2003, 22, 387.


34. Ong, T. G.; Yap, G.; Richeson, D. S. Formation of a Guanidinate-Supported Titanium Imido Complex: A Catalyst for Alkyne Hydroamination. Organometallics 2002, 21, 2839.


35. Ong, T. G.; Wood, D.; Yap, G.; Richeson, D. S. Transformations of Aryl Isocyanide on Guanidinate-Supported Organozirconium Complexes To Yield Terminal Imido, Iminoacyl, and Enediamido Ligands. Organometallics 2002, 21, 1.


36. Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Formation of a Guanidinate-Supported Titanium Imido Complex: A Catalyst for Alkyne Hydroamination. Organometallics 2002, 21, 2839.