Associate Professor Education Education: S.B. Massachusetts Institute of Technology, 2000 Ph.D. California Institute of Technology, 2005 Postdoc Stanford University, 2005-2008 Research Research Areas: Organic Chemistry Research Interests: 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 Selected Publications: 2022 Gall, B. K.; Smith, A. K.; Ferreira, E. M. Dearomative (3+2) Cycloadditions between Indoles and Vinyldiazo Species Enabled by a Red-Shifted Chromium Photocatalyst. Angewandte Chemie International Edition 2022, 61(45), e202212187. doi:10.1002/anie.202212187 Ke, Y. -T.; Gall, B. K.; Dewey, N. S.; Rotavera, B.; Ferreira, E. M. Multigram Synthesis of a Combustion-Relevant delta-Ketohydroperoxide through Sulfonylhydrazine Substitution. Chemistry a European Journal 2022, 28(62), e202202266. doi:10.1002/chem.202202266 Knutson, P. C.; Ji, H.; Harrington, C. M.; Ke, Y. -T.; Ferreira, E. M. Chirality Transfer and Asymmetric Catalysis: Two Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine. Organic Letters 2022, 24(27), 4971-4976. doi:10.1021/acs.orglett.2c01974 Knight, B. J.; Ferreira, E. M. Palladium/Norbornene Cooperative Catalytic C–H Functionalization. In Handbook of CH-Functionalization; Maiti, D., Ed.; Wiley-VCH GmbH, 2022. doi:10.1002/9783527834242.chf0002 2021 Ferreira, E. M.; Newcomb, E. T.; Knutson, P. C. Cycloisomerizations Across Three States: the Total Synthesis of Gelsenicine. In Strategies and Tactics in Organic Synthesis; Harmata, M., Ed.; Elsevier: Amsterdam, 2021; Vol. 15, pp 177-209. doi:10.1016/B978-0-12-822212-6.00005-9 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
