Education
- S.B. Massachusetts Institute of Technology, 2000
- Ph.D. California Institute of Technology, 2005
- Postdoc Stanford University, 2005-2008
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
2019
Costello, J. P.; Ferreira, E. M. Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O–H and N–H Additions. Organic Letters 2019, 21(24), 9934-9939. doi:10.1021/acs.orglett.9b03557
Ferreira, E. M. Decoration of Molecules Made Easy. Nature 2019, 567, 184-185. doi:10.1038/d41586-019-00767-w
2018
Knutson, P. C.; Fredericks, H. E.; Ferreira, E. M. Synthesis of 1,3-Diynes Via Cadiot-Chodkiewicz Coupling of Volatile, in Situ-Generated Bromoalkynes. Organic Letters 2018, 20(21), 6845-6849. doi:10.1021/acs.orglett.8b02975
Higgins, R. F.; Fatur, S. M.; Damrauer, N. H.; Ferreira, E. M.; Rappé, A. K.; Shores, M. P. Detection of an Energy-Transfer Pathway in Cr-Photoredox Catalysis. ACS Catalysis 2018, 8(10), 9216-9225. doi:10.1021/acscatal.8b03013
Sarabia, F. J.; Li, Q.; Ferreira, E. M. Cyclopentene Annulations of Alkene Radical Cations with Vinyl Diazo Species Using Photocatalysis. Angewandte Chemie International Edition 2018, 57(34), 11015-11019. doi:10.1002/anie.201805732
Shen, X.; Wang, J.; Gall, B. K.; Ferreira, E. M.; Yuan, Q.; Yan, Y. Establishment of Novel Biosynthetic Pathways for the Production of Salicyl Alcohol and Gentisyl Alcohol in Engineered Escherichia coli. ACS Synthetic Biology 2018, 7(4), 1012-1017. doi:10.1021/acssynbio.8b00051
2017
Wang, J.; Mahajani, M.; Jackson, S. L.; Yang, Y.; Chen, M.; Ferreira, E. M.; Lin, Y.; Yan, Y. Engineering a bacterial platform for total biosynthesis of caffeic acid derived phenethyl esters and amides. Metabolic Engineering 2017, 44, 89-99. doi:10.1016/j.ymben.2017.09.011
Seizert, C. A.; Ferreira, E. M. A boron-based Ireland-Claisen approach to the synthesis of pordamacrine A. Tetrahedron 2017, 73(29), 4186-4194. doi:10.1016/j.tet.2016.11.030
Li, Q.; Ferreira, E. M. Meta-Selective C−H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold. Chemistry - A European Journal 2017, 23(48), 11519-11523. doi:10.1002/chem.201703054
Sarabia, F. J.; Ferreira, E. M. Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis. Organic Letters 2017, 19(11), 2865-2868. doi:10.1021/acs.orglett.7b01095
Stevenson, S. M.; Higgins, R. F.; Shores, M. P.; Ferreira, E. M. Chromium photocatalysis: accessing structural complements to Diels-Alder adducts with electron-deficient dienophiles. Chemical Science 2017, 8(1), 654-660. doi:10.1039/c6sc03303b
Huynh, K. Q.; Seizert, C. A.; Ozumerzifon, T. J.; Allegretti, P. A.; Ferreira, E. M. Platinum-Catalyzed α,β-Unsaturated Carbene Formation in the Formal Syntheses of Frondosin B and Liphagal. Organic Letters 2017, 19(1), 294-297. http://doi.org/10.1021/acs.orglett.6b03682
2016
Stevenson, S. M.; Newcomb, E. T.; Ferreira, E. M. C–C Bond Migration in the Cycloisomerization of 1,6-Enynes. Organic Chemistry Frontiers 2016, 3, 1228-1335. http://doi.org/10.1039/c6qo00224b
Li, Q.; Knight, B. J.; Ferreira, E. M. Palladium(II)-Catalyzed ortho-Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold. Chemistry - A European Journal 2016, 22, 13054-13058. http://doi.org/10.1002/chem.201602844
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. http://doi.org/10.1021/jacs.6b02723
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. http://doi.org/10.1021/jacs.5b12263
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. http://doi.org/10.1039/c5sc03948g
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. http://doi.org/10.1021/acs.orglett.5b03246
2015
Knight, B. J.; Stache, E. E.; Ferreira, E. M. An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides. Tetrahedron 2015, 71, 5814 - 5823. http://doi.org/10.1016/j.tet.2015.05.010
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. http://doi.org/10.1002/anie.201501220
2014
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. http://doi.org/10.1021/ol403320d
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. http://doi.org/10.1002/chem.201304384
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. http://doi.org/10.1016/j.tet.2014.03.012
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. http://doi.org/10.1039/c3cc47499b
Ferreira, E. M. C–H Activation. A Surrogate for Selectivity. Nature Chemistry 2014, 6, 94-96. http://doi.org/10.1038/nchem.1851
2013
Newcomb, E. T.; Ferreira, E. M. Highly Enantiospecific Platinum-Catalyzed Cycloisomerizations: Synthesis of Enantioenriched Oxabicycloheptene Derivatives. Organic Letters 2013, 15, 1772 - 1775. http://doi.org/10.1021/ol400625f
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. http://doi.org/10.1002/anie.201303007
Allegretti, P. A.; Ferreira, E. M. Platinum-catalyzed cyclizations viacarbene intermediates: syntheses of complementary positional isomers of isoxazoles. Chem. Sci. 2013, 4, 1053 - 1058. http://doi.org/10.1039/c2sc21671j
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. http://doi.org/10.1021/ja408957a
2012
Rooke, D. A.; Ferreira, E. M. Palladium-Catalyzed Hiyama Couplings of α-Silylenoates and α-Silylenamides. Organic Letters 2012, 14, 3328 - 3331. http://doi.org/10.1021/ol301300r
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 - 1628. http://doi.org/10.1039/c2sc20176c
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. http://doi.org/10.1002/anie.201108714
2011
Allegretti, P. A.; Ferreira, E. M. Generation of α,β-Unsaturated Platinum Carbenes from Homopropargylic Alcohols: Rearrangements to Polysubstituted Furans. Organic Letters 2011, 13, 5924 - 5927. http://doi.org/10.1021/ol202649j
2010
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. http://doi.org/10.1021/ja1058197
