Keary Engle, PhD

Professor
Department of Chemistry


 Email

Scripps Research Joint Appointments

Faculty, Graduate Program

Research Focus

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.

Education

D.Phil. (Biochemistry), University of Oxford, 2013
Ph.D. (Chemistry), Scripps Research, 2013
B.S. (Chemistry, Economics, Mathematics, Statistics), University of Michigan, 2007

Professional Experience

2013-2015 NIH Postdoctoral Fellow, California Institute of Technology
2011-2011 NSF/JSPS EAPSI Fellow, The University of Tokyo
2008-2008 IDECAT Fellow, Stockholm University
2007-2008 J. William Fulbright Fellow, Max Planck Institute for Coal Research
2006-2006 DAAD RISE Fellow, University of Stuttgart

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

Selected References

All Publications

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 Nuclopalladation/Protodepalladation Approach,” Synlett 2017, 28, 2057–2065.

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.

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.

Liu, Z.; Derosa, J.; Engle, K. M. “Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group,” J. Am. Chem. Soc. 2016, 138, 13076–13081.

Gurak, J. A., Jr.; Yang, K. S.; Liu, Z.; Engle, K. M. “Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation,” J. Am. Chem. Soc. 2016, 138, 5805–5808.