Research Mission

Organic molecules make up nearly everything around us, including our medicines, clothing, and fuels. Research in organic chemistry is thus an essential pursuit that can impact many other scientific disciplines. By finding novel methods of building molecular architecture, we can facilitate the discovery of life-saving therapeutics, invention of novel materials, and search for alternative energies.

Our research mission is to invent better tools for organic synthesis, including new reagents, catalysts, and strategies. More specific goals include finding ways to directly convert carbon-hydrogen bonds into other functional groups, use carbon dioxide as a raw material, and make biologically active heterocycles. Our approach to these diverse challenges shares a common theme—to harness the power of transition metal catalysis and transform simple reagents into valuable products. Our work is motivated by
1) a fundamental interest in new organometallic pathways and 2) a practical need for more efficient and environmentally friendly technologies. We plan to use these methods to make natural products, pharmaceutical agents, and unique materials.

Students in the Dong Lab will be trained for future careers as synthetic organic chemists in academia and the pharmaceutical and fine chemical industry. For more information, see publications, invited contributions, highlights and reviews, and funding below. If you’re interested in joining our lab, please click here on how to apply.


Publications

Wu, X.; Riedel, J.; Dong, V. M. “Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis.” Angew. Chem. Int. Ed. 2017, Early View.



Cruz, F. A.+; Zhu, Y.+; Tercenio, Q. D.; Shen, Z.; Dong, V. M. “Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.” J. Am. Chem. Soc. 2017, 139, 10641.



Kim, D. K.; Riedel, J.; Kim, R. S.; Dong, V. M. “Cobalt Catalysis for Enantioselective Cyclobutanone Construction.” J. Am. Chem. Soc. 2017, 139, 10208.



Yang, X.-H.; Dong, V. M. “Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes.” J. Am. Chem. Soc. 2017, 139, 1774.



Cruz, F. A.; Dong, V. M. “Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.” J. Am. Chem. Soc. 2017, 139, 1029.



Le, D. N.+; Riedel, J.+; Kozlyuk, N.; Martin, R. W.; Dong, V. M. “Cyclizing Pentapeptides: Mechanism and Application of Dehydrophenylalanine as a Traceless Turn-Inducer.” Org. Lett. 2017, 19, 114.


Wu, X.; Chen, Z.; Bai, Y. B.; Dong, V. M. “Diastereodivergent Construction of Bicyclic ?-Lactones via Enantioselective Ketone Hydroacylation.” J. Am. Chem. Soc. 2016, 138, 12013.


Cruz, F. A.; Chen, Z.; Kurtoic, S. I.; Dong, V. M. “Tandem Rh-Catalysis: Decarboxylative Β-Keto Acid and Alkyne Cross-Coupling.” ChemComm 2016, 52, 5836.



Park, J. W.; Chen, Z.; Dong, V. M. “Rhodium-Catalyzed Enantioselective Cycloisomerization to Cyclohexenes Bearing Quaternary Carbon Centers.” J. Am. Chem. Soc. 2016, 138, 3310.



Chen, Q. A.; Chen, Z.; Dong, V. M. “Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.” J. Am. Chem. Soc. 2015, 137, 8392.


Read the highlight from C&EN News.

Park, J. W.; Kou, K. G. M.; Kim, D. K.; Dong, V. M. “A Rh-Catalyzed Desymmetrization of Quaternary Centers by Isomerization-Hydroacylation.” Chem. Sci. 2015, 6, 4479.



Chen, Q. A.; Cruz, F. A.; Dong, V. M. “Alkyne Hydroacylation: Switching Regioselectivity by Tandem Ruthenium Catalysis.” J. Am. Chem. Soc. 2015, 137, 3157.



Murphy, S. K.; Park, J.-W.; Cruz, F. A.; Dong, V. M. “Rh-catalyzed C-C bond cleavage by transfer hydroformylation.” Science 2015, 347, 56.


Thanks to Clark Landis for the perspective in Science.
Read the highlight from C&EN News.
Read the highlight in Korean from Dong-A Science.


Whittaker, A. M.; Dong, V. M. “Ni-Catalyzed Dehydrogenative Cross-Coupling: Direct Transformation of Aldehydes to Esters and Amides.” Angew. Chem. Int. Ed. 2015, 54, 1312.



Murphy, S. K.; Bruch, A.; Dong, V. M. “Mechanistic Insights into Hydroacylation with Non-chelating Aldehydes and 2-Vinylphenols.” Chem. Sci. 2015, 6, 174.


Oldenhuis, N. J.; Dong, V. M.; Guan, Z. “From Racemic Alcohols to Enantiopure Amines: Ru-Catalyzed Diastereoselective Amination.” J. Am. Chem. Soc. 2014, 136, 12548.


Kou, K. G. M.; Le, D. N.; Dong, V. M. “Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides.” J. Am. Chem. Soc. 2014, 136, 9471.


Chen, I.-H.; Kou, K. G. M.; Le, D. N.; Rathbun C. M.; Dong, V. M. “Recognition and Site-Selective Transformation of Monosaccharides Using Copper(II) Catalysis.” Chem. Eur. J. 2014, 20, 5013.


Read the highlight from SYNFACTS.


Chen, Q. A.; Kim, D. K.; Dong, V. M. “Regioselective Hydroacylation of 1,3-Dienes by Cobalt-Catalysis.” J. Am. Chem. Soc. 2014, 136, 3772.



Murphy, S. K.; Bruch, A.; Dong, V. M. “Substrate-Directed Hydroacylation: Rh-Catalyzed Coupling of Vinyl Phenols and Non-Chelating Aldehydes.” Angew. Chem. Int. Ed. 2014, 53, 2455.



Dornan, P. K.+; Kou, K. G. M.+; Houk K. N.; Dong, V. M. “Dynamic Kinetic Resolution of Allylic Sulfoxides by Rh-Catalyzed Hydrogenation: A Combined Theoretical and Experimental Mechanistic Study.” J. Am. Chem. Soc. 2014, 136, 291.



Murphy, S. K.; Dong, V. M. “Enantioselective Ketone Hydroacylation using Noyori's Transfer Hydrogenation Catalyst.” J. Am. Chem. Soc. 2013, 135, 5553.



von Delius, M.; Le, C. M.; Dong, V. M. “Rhodium-Phosphoramidite Catalyzed Alkene Hydroacylation: Mechanism and Octaketide Natural Product Synthesis.”
J. Am. Chem. Soc. 2012, 134, 15022
.



Murphy, S. K.; Coulter, M. M.; Dong, V. M. “β-Hydroxy Ketones Prepared by Regioselective Hydroacylation.” Chem. Sci. 2012, 3, 355.



Murphy, S. K.; Petrone, D. A.; Coulter, M. M.; Dong, V. M. “Catalytic Hydroacylation as an Approach to Homoaldol Products.” Org. Lett. 2011, 13, 6216.



Yeung, C. S.; Hsieh, T. H. H.; Dong, V. M. “Ru-catalyzed Activation of sp3 C–O Bonds: O- to N-Alkyl Migratory Rearrangement in Pyridines and Related Heterocycles.”
Chem. Sci. 2011, 2, 544
.

Top ten most accessed articles in December 2010.



Khan, H. A.; Kou, K. G. M.; Dong, V. M. “Nitrogen-directed Ketone Hydroacylation: Enantioselective Synthesis of Benzoxazepinones and Benzoxazecinones.”
Chem. Sci. 2011, 2, 407
.

Featured on the cover with artwork by Peter Dornan.
Top ten most accessed articles in December 2010.



Zhao, X.; Dong, V. M. “Carbon-Sulfur Reductive Elimination from Pd(IV) Sulfinate Complexes.” Angew. Chem. Int. Ed. 2011, 50, 932.



Coulter, M. M.; Kou, K. G. M.; Galligan, B.; Dong, V. M. “Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides.” J. Am. Chem. Soc. 2010, 132, 16330.


Editorial Board of SYNFACTS selects this article as the Synfact of the month.


Phan, D. H. T.; Kou, K. G. M.; Dong, V. M. “Enantioselective Desymmetrization of Cyclopropenes by Hydroacylation.” J. Am. Chem. Soc. 2010, 132, 16354.



Editorial Board of SYNFACTS selects this article as the Synfact of the month.


Coulter, M. M.; Dinglasan, J.; Goh, J. B.; Nair, S.; Anderson, D. J.; Dong, V. M. “Preparing Water-Dispersed Palladium Nanoparticles via Polyelectrolyte Nanoreactors.” Chem. Sci. 2010, 1, 772.


Read the highlight from Chemical Science Blog.


Yeung, C. S.; Zhao, X.; Borduas, N.; Dong, V. M. “Pd-Catalyzed ortho-Arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate.” Chem. Sci. 2010, 1, 331.



Top ten most accessed articles in August 2010.

Zhao, X.; Yeung, C. S.; Dong, V. M. “Palladium-Catalyzed Ortho-Arylation of O-Phenylcarbamates with Simple Arenes and Sodium Persulfate.” J. Am. Chem. Soc. 2010, 132, 5837.



Editorial Board of SYNFACTS selects this article as the Synfact of the month.


Li, Y.; Jardine, K. J.; Tan, R.; Song, D.; Dong, V. M. “Palladium-Catalyzed Intramolecular Carboesterification of Olefins: A Formal [3+2] Cycloaddition.” Angew. Chem. Int. Ed. 2009, 48, 9690.

Selected by the editors as a "Hot Paper".


Phan, D. H. T.; Kim, B.; Dong, V. M. “Phthalides by Rhodium-Catalyzed Ketone Hydroacylation.”
J. Am. Chem. Soc. 2009, 131, 15608
.

Read the highlight from SYNFACTS.
Read the highlight in Angewandte by Michael Willis.

Coulter, M. M.; Dornan, P. K.; Dong, V. M. “Rh-Catalyzed Intramolecular Olefin Hydroacylation: Enantioselective Synthesis of Seven- and Eight-Membered Heterocycles.”
J. Am. Chem. Soc. 2009, 131, 6932.



Read the highlight from SYNFACTS.


Zhao, X.; Dimitrijević, E.; Dong, V. M. “Palladium-Catalyzed C–H Bond Functionalization with Arylsulfonyl Chlorides.” J. Am. Chem. Soc. 2009, 131, 3466.



Shen, Z.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. “Mechanistic Insights into the Rhodium-Catalyzed Intramolecular Ketone Hydroacylation.” J. Am. Chem. Soc. 2009, 131, 1077.



Shen, Z.; Dong, V. M. “Benzofurans Prepared by C-H Bond Functionalization with Acylsilanes.” Angew. Chem. Int. Ed. 2009, 48, 784.



Read the highlight from SYNFACTS.



Yeung, C. S.; Dong, V. M. “Beyond Aresta’s Complex: Ni- and Pd-Catalyzed Organozinc Coupling to CO2.” J. Am. Chem. Soc. 2008, 130, 7826.

Read the highlight from SYNFACTS.
Read the highlight in Angewandte by Martin and Correa.

Li, Y.; Song, D.; Dong, V. M. “Palladium-Catalyzed Olefin Dioxygenation.”
J. Am. Chem. Soc. 2008, 130, 2962.

Read the highlight from SYNFACTS.



Shen, Z.; Khan, H. A.; Dong, V. M. “Rh-Catalyzed Carbonyl Hydroacylation: An Enantioselective Approach to Lactones.” J. Am. Chem. Soc. 2008, 130, 2916.



See the highlight in Chemistry World featuring this work: James Mitchell Crow, "Rhodium fast tracks route to lactones."
Editorial Board of SYNFACTS selects this article as the Synfact of the month.


Invited Contributions

von Delius, M.; Le, C. M.; Ellinger, B.; Kuzikov, M.; Gul, S.; Dong, V. M. “Synthesis and Biological Activity of Octaketides from the Cytosporone Family.” Isr. J. Chem. 2017, Early View.



Invited contribution in honor of Robert Bergman's Wolf Prize.


Kou, K. G. M.; Longobardi, L. E.; Dong, V. M. “Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes.” Advanced Synthesis & Catalysis 2015, 357, 2233.




Invited contribution in honor of Stephen Buchwald.


Oldenhuis, N. J.; Dong, V. M.; Guan, Z. “Catalytic acceptorless dehydrogenations: Ru-Macho catalyzed construction of amides and imines.” Tetrahedron 2014, 70, 4213.




Invited contribution in honor of Sarah Reisman.


Phan, D. H. T.; Dong, V. M. “Silver-catalyzed ring-opening of cyclopropenes: preparation of tertiary α-branched allylic amines.” Tetrahedron 2013, 69, 5726.




Invited contribution in honor of Melanie Sanford.


Dornan, P. K.; Leung, P. L.; Dong, V. M. “Synthesis of C3- and C2-symmetric tris- and bis-sulfoxide ligands by asymmetric oxidation.” Tetrahedron 2011, 67, 4378.



Invited contribution in honor of Dean Toste.


Borduas, N.; Lough, A. J.; Dong, V. M. “Cyclopalladation of N-Phenylbenzamides: Synthesis and Structure of Bimetallic Palladium(II)-Complexes.” Inorg. Chem. Acta. 2011, 369, 247.



Invited contribution in honor of Robert Bergman.


Yeung, C. S.; Dong, V. M. ”Pd-catalyzed ortho-Arylation of N-Aryloxazolidinones with Simple Arenes Using Sodium Persulfate.” Synlett. 2011, 7, 974.




Invited contribution in honor of Xiyan Lu and Li-Xin Dai.


Hsieh, T. H. H.; Dong, V. M. “Indole Synthesis: Palladium-Catalyzed C–H Bond Amination via Reduction of Nitroalkenes with Carbon Monoxide.” Tetrahedron 2009, 65, 3062.



Invited contribution in honor of Justin Du Bois's Young Investigator Award.




Highlights and Reviews

Kim, D. K.; Dong, V. M. “An Enlightening Reactor.” ACS Cent. Sci. 2017, 3, 526


Dornan, P. K.; Dong, V. M. “Vinylation Using a Palladium Catalyst” in Science of Synthesis: Catalytic Transformations via C-H Activation Vol. 1, Yu, J-Q; Thieme: Germany, 2016; Chapter 5.


Kou, K. G. M.; Dong, V. M. “Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis.” Org. Biomol. Chem. 2015, 13, 5844.








Murphy, S. K.; Dong, V. M. “Catalytic Enantioselective hydroacylation of olefins with rhodium catalysts.” Chem. Commun. 2014, 50, 13645.








Yeung, C. S.; Dong, V. M. “Making C-C Bonds from Carbon Dioxide via Transition-Metal Catalysis.” Topics in Catalysis. 2014, 57, 1342.








Coulter, M. M.; Dong, V. M. “Transition Enantioselective Synthesis of Lactones via Rh-Catalyzed Ketone Hydroacylation” in Asymmetric Synthesis II: More Methods and Applications, M. Christmann; S. Brase; Wiley-VCH: New York, 2012; Chapter 35.


Gladysz, J.; Ball, Z. T.; Bertrand, G.; Blum, S. A.; Dong, V. M.; Dorta, R.; Hahn, F. E.; Humphrey, M. G.; Jones, W. D.; Klosin, J.; Manners, I.; Marks, T. J.; Mayer, J. M.; Rieger, B.; Ritter, J. C.; Sattelberger, A. P.; Schomaker, J. M.; Yam V. W. “Organometallics Roundtable 2011.” Organometallics 2012, 31, 1.






Yeung, C. S.; Dong, V. M. “Catalytic Dehydrogenative Cross-Coupling: Forming Carbon-Carbon Bonds by Oxidizing Two Carbon-Hydrogen Bonds.” Chem. Rev. 2011, 111, 1215.







For a thematic issue: Frontiers in Transition Metal Catalyzed Reactions.


Yeung, C. S.; Dong, V. M. “A New Direction in Enantioselective Catalysis: Scaffolding Ligands in Olefin Hydroformylation”, Highlight article, Angew. Chem. Int. Ed. 2011, 50, 809.


Yeung, C. S.; Dornan, P. K.; Dong, V. M. “Transition Metal Catalyzed Approaches to Lactones Involving C-O Bond Formation” in Catalyzed Carbon-Heteroatom Bond Formation, A. K. Yudin; Wiley-VCH: New York, 2010; Chapter 2.



Funding



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