Current Research

Organic Chemistry

 

Research in our group is focused on the development of new synthetic transformations, primarily centered around transition metal catalysis.  Critical to the invention of these methods is our ability to derive inspiration from both reaction mechanisms and natural products.  Our understanding of intermediates along mechanistic pathways allows us to design innovative chemcial transformations that can capitalize on these potentially reactive species.  Concurrently, we are interested in natural products and other molecules possessing interesting structural properties and biological activity.  Our analyses of their respective core molecular architectures initiates the design of these synthetically important methods.  These sources of inspiration continuously feed into our logical advancement of synthetic methods.  At the same time, our expansion of the synthetic toolbox affords us opportunities for applications of these methods, both in mechanistic studies and in natural product synthesis. 

 

Current efforts in our group are primarily dedicated toward three distinct areas: catalytic alkyne activation, directed catalytic C–H functionalization, and light-activated catalysis based on earth-abundant reagents.  In all of these areas, fundamental questions of reaction design and potential applications are probed.  Ultimately, we anticipate that our explorations in these and other conceptual areas will eventually deepen our understanding of many principles of catalysis and reactivity.

 

Selected Publications

Knight, B. J. ; Rothbaum, J. O. ; Ferreira, E. M. The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols. Chem. Sci. 2016, 7, 1982 - 1987.
Allegretti, P. A. ; Huynh, K. ; Ozumerzifon, T. J. ; Ferreira, E. M. Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene. Organic Letters 2016, 18, 64 - 67.
Newcomb, E. T. ; Knutson, P. C. ; Pedersen, B. A. ; Ferreira, E. M. Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy. Journal of the American Chemical Society 2016, 138, 108 - 111.
Higgins, R. F. ; Fatur, S. M. ; Shepard, S. G. ; Stevenson, S. M. ; Boston, D. J. ; Ferreira, E. M. ; Damrauer, N. H. ; Rappé, A. K. ; Shores, M. P. Uncovering the Roles of Oxygen in Cr(III) Photoredox Catalysis. Journal of the American Chemical Society 2016, 138, 5451 - 5464.
Stevenson, S. M. ; Shores, M. P. ; Ferreira, E. M. Photooxidizing Chromium Catalysts for Promoting Radical Cation Cycloadditions. Angewandte Chemie International Edition 2015, 54, 6506 - 6510.
Knight, B. J. ; Stache, E. E. ; Ferreira, E. M. Complementary Stereochemical Outcomes in Proline-Based Self-Regenerations of Stereocenters. Organic Letters 2014, 16, 432 - 435.
Seizert, C. A. ; Ferreira, E. M. An Examination of the Scope and Stereochemistry of the Ireland-Claisen Rearrangement of Boron Ketene Acetals. Chemistry - A European Journal 2014, 20, 4460 - 4468.
Rooke, D. A. ; Menard, Z. A. ; Ferreira, E. M. An analysis of the influences dictating regioselectivity in platinum-catalyzed hydrosilylations of internal alkynes. Tetrahedron 2014, 70, 4232 - 4244.
Stevenson, S. M. ; Newcomb, E. T. ; Ferreira, E. M. C–C bond migration in the cycloisomerization of oxygen-tethered 1,6-enynes. Chem. Commun. 2014, 50, 5239 - 5241.
Barczak, N. T. ; Rooke, D. A. ; Menard, Z. A. ; Ferreira, E. M. Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen-Induced 1,2-Silyl Migration. Angewandte Chemie International Edition 2013, 52, 7579 - 7582.
Allegretti, P. A. ; Ferreira, E. M. Vicinal Bisheterocyclizations of Alkynes via Nucleophilic Interception of a Catalytic Platinum Carbene. Journal of the American Chemical Society 2013, 135, 17266 - 17269.
Rooke, D. A. ; Ferreira, E. M. Platinum-Catalyzed Hydrosilylations of Internal Alkynes: Harnessing Substituent Effects to Achieve High Regioselectivity. Angewandte Chemie International Edition 2012, 51, 3225 - 3230.
Stache, E. E. ; Seizert, C. A. ; Ferreira, E. M. Molecular scaffolds with remote directing groups for selective palladium-catalyzed C–H bond functionalizations. Chemical Science 2012, 3, 1623.
Rooke, D. A. ; Ferreira, E. M. Palladium-Catalyzed Hiyama Couplings of α-Silylenoates and α-Silylenamides. Organic Letters 2012, 14, 3328 - 3331.
Rooke, D. A. ; Ferreira, E. M. Stereoselective Syntheses of Trisubstituted Olefins via Platinum Catalysis: α-Silylenones with Geometrical Complementarity. Journal of the American Chemical Society 2010, 132, 11926 - 11928.