Arthur F. Thurnau, Margaret and Herman Sokol Professor in Medicinal or Synthetic Chemistry and Arthur F. Thurnau Professor of Chemistry
About
The long-standing focus of the Montgomery group has been the discovery and development of new transition metal-catalyzed reactions that enable the efficient assembly of bioactive structures. These 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. Our laboratory played a pioneering role in developing the area of nickel-catalyzed reductive coupling methods involving reactive pi-components, and we have provided mechanistic understanding and numerous preparative advances in this field. Recent work has focused on developing a broad array of regiodivergent catalytic transformations, where two or more product regioisomers may be obtained through careful control of catalyst structure and reaction conditions. Additionally, new catalytic cycloaddition and C-H activation processes are currently being developed.
Our laboratory has recently initiated a program in the development of innovative catalytic methods for glycoside bond construction. A new class of carbohydrate-derived reagents, termed sugar silanes, was devised in our laboratory and enables sequential reductive conversions paired with an intramolecular glycosylation process. Our most recent thrust involves boron-catalyzed glycosylations including multicomponent iterative couplings. A collaborative interest is the development of biocatalysts as general tools in synthetic chemistry, particularly for the functionalization of unactivated C-H bonds. Our recent studies demonstrate that carefully designed substrate modifications enable improvements and/or reversals in site-selectivity of oxidations of a broad array of unnatural substrates using engineered cytochrome P450 enzymes.
Our general approach to research encompasses identifying novel catalyst structures that accomplish unprecedented 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
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.
Rand, A. W.; Yin, H.; Xu, L., Giacoboni, J.; Martin-Montero, R.; Romano, C.; Montgomery, J.; Martin, R. “A Dual Catalytic Platform for Enabling sp3 alpha-C-H Arylation and Alkylation of Benzamides” ACS Catal. 2020, 10, 4671-4676.
Rand, A. W.; Montgomery, J. “Catalytic Reduction of Aryl Trialkylammonium Salts to Aryl Silanes and Arenes” Chem. Sci. 2019, 10, 5338-5344.
Wiensch, E. M.; Montgomery, J. “Nickel-Catalyzed Amination of Silyloxyarenes through C–O Bond Activation” Angew. Chem. Int. Ed. 2018, 57, 11045-11049.
Nett, A. J.; Canellas, S.; Higuchi, Y.; Robo, M.; Kochkodan, J. M.; Haynes, M. T.; Kampf, J. W.; Montgomery, J. “Stable, Well-Defined Nickel(0) Catalysts for Catalytic C–C and C–N Bond Formation” ACS Catal. 2018, 8, 6606-6611.
Shimkin, K. W.; Montgomery, J. “Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling” J. Am. Chem. Soc. 2018, 140, 7074-7078.
Gilbert, M. M.; DeMars II, M. D.; Yang, S.; Grandner, J. M.; Wang, S.; Wang, H.; Narayan, A. R. H.; Sherman, D. H.; Houk K. N.; Montgomery, J. “Synthesis of Diverse 11- and 12-Membered Macrolactones from a Common Linear Substrate Using a Single Biocatalyst” ACS Cent. Sci. 2017, 3, 1304-1310.
Research Areas(s)
- Organic Chemistry
- Organometallic Chemistry
- Carbohydrate Chemistry
- Catalysis
Award(s)
- 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
