Associate Professor of Chemistry
Ph.D. Harvard University, 2004
(Organic and Organometallic Chemistry)
The main focus of the Lalic group is the development of practical transition-metal catalyzed transformations that address problems encountered in the synthesis of complex organic molecules. Our approach to reaction development will involve the synthesis of new transition-metal complexes, the systematic study of their reactivity, and the detailed exploration of reaction mechanisms. Finally, the utility of the transformations pioneered in our group will be demonstrated by the expedient total synthesis of complex organic molecules.
Our focus on both practical and fundamental aspects of reaction development provides an opportunity for students in the group to get training and expertise in various aspects of organometallic, physical organic, and synthetic organic chemistry.
Enantioselective Fragment Coupling Reactions
The development of catalytic cross-coupling and enantioselective functionalization reactions in the last thirty years has revolutionized organic synthesis. One of the current challenges in organometallic chemistry and organic synthesis is the development of transformations that lead to both the increase in molecular complexity through fragment coupling and the concomitant enantioselective functionalization. Developing transformations of this type, such as carbohydroxylation of alkenes, is one of the main goals of our research.
Transition Metal-Catalyzed Transformations of Strained Heterocycles
Strained heterocycles, being readily available and thermodynamically unstable, are ideal yet underexploited substrates in metal-catalyzed transformations. Our goal is to explore the opportunities these molecules provide and discover new transformations that will be useful in synthesis of complex organic molecules.
Natural Product Synthesis
The synthesis of natural products is an important part of our group's research. Our choice of target molecules allows us to test the scope and utility of our methodologies, and provides inspiration for new ones.
Uehling, M. R.; Rucker, R. P.; Lalic, G. "Catalytic Anti-Markovnikov Hydrobromination of Alkynes." J. Am. Chem. Soc. 2014, 136, 8799-8803.
Dang, H.; Mailig, M.; Lalic, G.
"Mild Copper-Catalyzed Fluorination of Alkyl Triflates with Potassium Fluoride." Angew. Chem., Int. Ed. 2014, 53, 6473-6476.
Cox, N.; Dang, H.; Whittaker, A. M.; Lalic, G. "Mild Copper-Catalyzed Fluorination of Alkyl Triflates with Potassium Fluoride." Tetrahedron 2014, 27-28, 4219-4231.
Dang, H.; Cox, N.; Lalic, G. "Copper-Catalyzed Reduction of Alkyl Triflates and Iodides: An Efficient Method for the Deoxygenation of Primary and Secondary Alcohols." Angew. Chem., Int. Ed. 2014, 53, 752.
Cox, N.; Uehling, M. R.; Haelsig, K. T.; Lalic, G. "Catalytic Asymmetric Synthesis of Cyclic Ethers Containing an α-Tetrasubstituted Stereocenter." Angew. Chem., Int. Ed. 2013, 52, 4878. (Highlighted in SYNFACTS)
Whittaker, A. M.; Lalic, G.
"Monophasic Catalytic System for the Selective Semireduction of Alkynes." Org. Lett. 2013, 15, 1113. (Highlighted in SYNFACTS)
Rucker, R. P.; Lalic, G.
"Copper-Catalyzed Electrophilic Amination of Organoboron Compounds." Synlett 2013, 24, 269. (invited synpacts article)
Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. "Synthesis of Tertiary Alkyl Amines from Terminal Alkenes: Copper-Catalyzed Amination of Alkyl Boranes." J. Am. Chem. Soc. 2012, 134, 6571.
Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. "Synthesis of Hindered Anilines: Copper-Catalyzed Electrophilic Amination of Aryl Boronic Esters." Angew. Chem., Int. Ed. 2012, 51, 3953.
Uehling, M. R.; Marionni, S. T.; and Lalic, G. "Asymmetric Synthesis of Trisubstituted Allenes: Copper-Catalyzed Alkylation and Arylation of Propargylic Phosphates." Org. Lett. 2012, 14, 362.
Awards & Activities