D.Phil., Biochemistry, University of Oxford, 2013
Ph.D., Chemistry, The Scripps Research Institute, 2013
B.S., Chemistry, Economics, Mathematics, and Statistics, University of Michigan, 2007
NIH Postdoctoral Research Fellow, California Institute of Technology (2013–2015)
Fulbright Fellow, Max-Planck-Institut für Kohlenforschung (2007–2008)
Awards & Professional Activities
Donald E. and Delia B. Baxter Foundation Young Faculty Award, 2016
Thomson Reuters Highly Cited Researcher, 2015–2016
IUPAC-Solvay International Award for Young Chemists, 2014
Ruth L. Kirschstein National Research Service Award (NIH F32), 2014–2015
Lincoln College Senior Scholarship, 2012–2013
Kenneth G. Hancock Memorial Student Award (ACS GCI), 2012
Roche Excellence in Chemistry Award, 2012
Patricia Cross Future Leaders Award (AAC&U), 2011
Jairo H. Arévelo Fellowship (TSRI), 2010–2011
Joseph Breen Memorial Fellowship,(ACS GCI), 2010
Skaggs Oxford Scholarship, 2008–2013
NSF Graduate Research Fellowship, 2008–2013
NDSEG Fellowship, 2008–2011
TSRI Deans’ Fellowship, 2008–2009
Fulbright Scholarship (with M. T. Reetz), 2007–2008
American Institute of Chemists Alumni Award, 2007
Eugene Sullivan Scholarship in Chemistry (UM Chemistry), 2007
Eli Lilly Organic Chemistry Award, 2006
ACS Analytical Chemistry Alumni Award, 2006
Jack Meiland Prize (UM Honors Program), 2006
Ernest Sims Prize in Economics (UM Economics), 2006
Telluride Association Residential Scholarship, 2004–2007
Organic small molecules make up the vast majority of medicines, biological probes, agrochemicals, and materials building blocks. Thus, though they are ubiquitous in modern society, many classes of small molecules remain problematic to prepare using conventional methods. Contemporary synthetic routes routinely require multiple steps, generate large quantities of waste, or require substantial human energy to troubleshoot. Research in the Engle group focuses on addressing these challenges by harnessing the power of catalysis. Our group's goal is to advance the efficiency, effectiveness, and sustainability of chemical synthesis. The projects that we tackle are highly interdisciplinary, and as a consequence, students complement their core training in synthetic organic, physical organic, and organometallic chemistry with expertise in related disciplines in and outside of chemistry.
O’Duill, M. L.; Engle, K. M. “Protodepalladation as a Strategic Elementary Step in Catalysis,” Submitted (Invited Review).
Tran, V. T.; Gurak, J. A., Jr.; Yang, K. S.; Engle, K. M. “Activation of Diverse Carbon–Heteroatom and Carbon–Carbon Bonds via Palladium(II)-Catalyzed β-X Elimination,” Nat. Chem. 2018, In Press.
Gurak, J. A., Jr.; Engle, K. M. “Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling,” ChemRxiv 2018, DOI: 10.26434/chemrxiv.6619223.
Gao, D.-W.; Vinogradova, E. V.; Nimmagadda, S. K. †; Medina, J. M.†; Xiao, Y.; Suciu, R. M.; Cravatt, B. F.; Engle, K. M. “Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes,” J. Am. Chem. Soc. 2018, 140, 8069–8073. (†Authors contributed equally).
Zeng, T.; Liu, Z.; Schmidt, M. A.; Eastgate, M. D.; Engle, K. M. “Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System,” Org. Lett. 2018, 20, 3853–3857.
Derosa, J.; Tran, V. T.; van der Puyl; V. A.; Engle, K. M. “Carbon–Carbon π-Bonds as Conjunctive Reagents in Cross-Coupling,” Aldrichimica Acta 2018, 51, 21–32. (Invited review article).
Matsuura, R.; Jankins, T. C.; Yang, K. S.; Gallego, G. M.; Yang. S.; He, M.; Wang, F.; Marsters, R.; McAlpine, I.; Engle, K. M. “Palladium(II)-Catalyzed γ-Selective Hydroarylation of Alkenyl Carbonyl Compounds with Arylboronic Acids,” ChemRxiv 2018, DOI: 10.26434/chemrxiv.5885203.
Derosa, J.; van der Puyl; V. A.; Tran, V. T.; Liu, M.; Engle, K. M. “Directed Nickel-Catalyzed 1,2-Dialkylation of Alkenyl Carbonyl Compounds,” Chem. Sci. 2018, 9, 5278–5283.
Liu, M.; Yang, P.; Karunananda, M. K.; Wang, Y.; Liu, P.; Engle, K. M. “C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis,” J. Am. Chem. Soc. 2018, 140, 5805–5813.
Gao, D.-W.; Xiao, Y.; Liu, M.; Liu, Z.; Karunananda, M. K.; Chen, J. S; Engle, K. M. “Catalytic, Enantioselective Synthesis of Allenyl Boronates,” ACS Catal. 2018, 8, 3650–3654.
Derosa, J.†; O’Duill, M. L.†; Holcomb, M.; Boulous, M. N.; Patman, R. L.; Wang, F.; Tran-Dubé, M.; McAlpine, I.; Engle, K. M. “Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Aza-Heterocycles,” J. Org. Chem. 2018, 83, 3417–3425. (†Authors contributed equally).
Liu, Z.; Ni, H.-Q.; Zeng, T.; Engle, K. M. “Catalytic Carbo- and Aminoboration of Alkenyl Carbonyl Compounds via 5- and 6-Membered Palladacycles,” J. Am. Chem. Soc. 2018, 140, 3223–3227.
O’Duill, M. L.; Matsuura, R.; Wang, Y.; Turnbull, J. L.; Gurak, J. A., Jr.; Gao, D.-W.; Lu, G.; Liu, P.; Engle, K. M. “Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization,” J. Am. Chem. Soc. 2017, 139, 15576–15579.
Gurak, J. A., Jr.; Engle, K. M. “Regioselective Hydroamination Using a Directed Nucleopalladation/Protodepalladation Approach,” Synlett 2017, 28, 2057–2065. (Invited Synpact).
Liu, Z.; Wang, Y.; Wang, Z.; Zeng, T.; Liu, P.; Engle, K. M. “Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation,” J. Am. Chem. Soc. 2017, 139, 11261–11270.
Derosa, J.†; Tran, V. T.†; Boulous, M. N.; Chen, J. S.; Engle, K. M. “Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling,” J. Am. Chem. Soc. 2017, 139, 10657–10660. (†Authors contributed equally).
Gurak, J. A., Jr.; Tran, V. T.; Sroda, M. M.; Engle, K. M. “N-Alkylation of 2-Pyridone Derivatives via Palladium(II)-Catalyzed Directed Alkene Hydroamination,” Tetrahedron 2017, 73, 3636–3642. (Special Issue for Ang Li’s TYIA.)
Derosa, J.; Cantu, A. L.; Boulous, M. N.; O’Duill, M. L.; Turnbull, J. L.; Liu, Z.; De La Torre, D. M.; Engle, K. M. “Directed Palladium(II)-Catalyzed anti-Hydrochlorination of Unactivated Alkynes with HCl,” J. Am. Chem. Soc. 2017, 139, 5183–5193.
Liu, Z.; Zeng, T.; Yang, K. S.; Engle, K. M. “β,γ-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation,” J. Am. Chem. Soc. 2016, 138, 15122–15125.
Yang, K.; Gurak, J. A., Jr.; Liu, Z.; Engle, K. M. “Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Diverse C–H Nucleophiles,” J. Am. Chem. Soc. 2016, 138, 14705–14712.