Margaret and Herman Sokol Professor of Synthetic Chemistry and Arthur F. Thurnau Professor of Chemistry
(he/him)
About
The primary goal of the Montgomery group is the discovery and development of new catalytic reactions that provide new strategic disconnections for synthetic chemistry. Our efforts include the design and synthesis of new classes of transition metal catalysts, the discovery of new metal-catalyzed processes as enabling tools for organic synthesis, mechanistic and kinetic study of catalytic processes, and total synthesis of complex molecules and bioactive structures.
A major segment of our current effort focuses on the development of new nickel-catalyzed processes for derivatizing simple functional groups and/or unactivated C-H bonds. In one area, we are developing a suite of new synthetic processes for aldehyde additions that avoid the requirement of generating metalated nucleophiles such as Grignard reagents. Through the strategy we have developed, a wide array of functional groups including redox-active esters, alkyl bromides, epoxides and alkyl tosylates can undergo direct addition to aldehydes under reductive conditions. Current work is extending this strategy to include the direct addition of unactivated C-H bonds to carbonyl substrates through site-selective C-H activation.
A second major focus of our work involves the development of boron-catalyzed glycosylation processes. Our lab recently reported an efficient catalytic method for the stereoselective creation of glycosidic bonds, and the strategy has been tuned to allow iterative glycosylation, where complex tri- and tetrasaccharides can be efficiently assembled in one step from monosaccharide precursors. Our work in this area includes addressing fundamental methodological advances in catalytic glycosylation as well as the development of collaborative ventures in in the areas of glycobiology and glycomaterials.
Our general approach to research encompasses identifying novel catalyst structures that accomplish new chemical transformations, rigorously characterizing the mechanisms by which the processes occur, and optimizing the efficiency and selectivity of the processes developed. Attention is then placed on complex synthetic applications including natural product synthesis, assembly of novel glycosylated structures, and preparation of unnatural motifs designed to probe questions in biology and medicinal chemistry.
Representative Publications (full list here)
Rand, A. W.; Chen, M.; Montgomery, J. “Investigations into Mechanism and Origin of Regioselectivity in the Metallaphotoredox-Catalyzed α-Arylation of N-Alkylbenzamides” Chem. Sci. 2022, 13, 10566-10573.
Chen, M.; Montgomery, J. “Nickel-Catalyzed Heteroaromatic C-H Alkylation via Ligand-to-Ligand Hydrogen Transfer” ACS Catal. 2022, 18, 11015-11023.
Martin, J. L.; Sati, G. C.; Malakar, T.; Hatt, J.; Zimmerman, P. M.; Montgomery, J. “Glycoside Metathesis: Suppressing or Embracing Side Reactivity in Catalytic Glycosylations” J. Org. Chem. 2022, 87, 5817-5826
Xiao, J.; Li, Z.; Montgomery, J. “Nickel-Catalyzed Decarboxylative Coupling of Redox-Active Esters with Aliphatic Aldehydes,” J. Am. Chem. Soc. 2021, 143, 21234-21240.
Cruz, C. L.; Montgomery, J. “Nickel-Catalyzed Reductive Coupling of Unactivated Alkyl Bromides and Aliphatic Aldehydes” Chem. Sci. 2021, 12, 11995-12000.
Sati, G. C.; Martin, J. L.; Xu, Y.; Malakar, T.; Zimmerman, P. M.; Montgomery, J. “Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation” J. Am. Chem. Soc. 2020, 142, 7235-7242.
Research Areas(s)
- Organic Chemistry
- Organometallic Chemistry
- Catalysis
- C-H Activation
- Carbohydrate Chemistry
Award(s)
- NSF Special Creativity Award
- American Association for the Advancement of Science Fellow
- ACS Arthur C. Cope Scholar Award
- Camille Dreyfus Teacher Scholar Award
- Johnson and Johnson Focused Giving Grantee
- National Science Foundation Career Award
