个人简介

Levi was born in Bismarck, North Dakota in 1979. He grew up in Washburn, North Dakota and graduated from Washburn High School in 1997. He received his B.A. in Chemistry from Augustana College in Sioux Falls, SD in 2001, where he worked with Professor Gary Earl and Professor Jetty Duffy-Matzner. In 2002, he began his graduate studies with Professor Mukund P. Sibi at North Dakota State University. There he developed enantioselective dipolar cycloaddition reactions and applications of chiral relay ligands and auxiliaries in enantioselective catalysis. He received his Ph.D. in 2007 and moved to the University of Illinois, Urbana-Champaign to begin an NIH Postdoctoral Fellowship with Professor John F. Hartwig. At the U of I he developed a variety of enantioselective, iridium-catalyzed allylic substitution reactions. In 2011, he received an NIH Pathways to Independence Award (K99/R00) to develop new strategies to generate artificial metalloenzymes with Professor Huimin Zhao and Professor Hartwig. In January of 2012, he joined the Chemistry Department at Iowa State University as an Assistant Professor.

研究领域

Organic and Organometallic Chemistry/Catalysis/and Asymmetric Synthesis

Research in the Stanley Laboratory focuses on the identification of catalysts and the development of synthetic methods that streamline the synthesis of medicinally and industrially important molecules. Areas of interest include: 1) the development of new metal-catalyzed alkene functionalization reactions; 2) the development of new synthetic methods to form and functionalize heterocycles; and 3) the identification and development of catalysts that lie at the interface of traditional homogeneous and heterogeneous catalysis. Students in the Stanley group learn synthetic organic chemistry, heterocyclic chemistry, catalytic reaction development, asymmetric synthesis and catalysis, and materials synthesis and characterization. These skills are leveraged to address challenges in the development of new alkene hydroacylation and carboacylation reactions, the synthesis of quaternary carbon stereocenters, the synthesis of metal-organic frameworks (MOFs) and covalent organic frameworks (COFs), and the application of MOFs and COFs as catalysts of valuable organic reactions.

近期论文

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Tran, H. N.; Burgett, R. W.; Stanley, L. M. “Nickel-Catalyzed Asymmetric Hydroarylation of Vinylarenes: Direct Enantioselective Synthesis of Chiral 1,1-Diarylethanes” J. Org. Chem. 2021, 86, 3836–3849. DOI: 10.1021/acs.joc.0c02556 Koeritz, M. T.; Burgett, R. W.; Kadam, A. A.; Stanley, L. M. “Ni-Catalyzed Intermolecular Carboacylation of Internal Alkynes via Amide C–N Bond Activation” Org. Lett. 2020, 22, 5731–5736. DOI: 10.1021/acs.orglett.0c01607 Heintz, P. M.; Schumacher, B. P.; Chen, M.; Huang, W.; Stanley, L. M. “A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones” ChemCatChem. 2019, X, XX–XX.DOI: 10.1002/cctc.201900894 Kadam, A. A.; Metz, L. T.; Qian, Y.; Stanley, L. M. “Ni-Catalyzed Three-Component Alkene Carboacylation Initiated by Amide C-N Bond Activation” Acs Catal. 2019, 9, 5651–5656. DOI: 10.1021/acscatal.9b01620 Metz, L. T.; Leng, M.; Evans, J.; Stanley, L. M. “Synthesis of heteroarylated ketones via bismuth(III) triflate-promoted regioselective 1,4- and 1,6-additions of electron-rich heteroarenes to cyclic enones and dienones” Tetrahedron. 2018, 26, 328-3292. DOI: 10.1016/j.tet.2018.04.002 Metz, L. T.; Lutovsky, A. G.; Stanley, L. M. “An Acid-Catalyzed Addition and Dehydration Sequence for the Synthesis of Heteroarylated Steroidal Dienes” J. Org. Chem. 2018, 83, 1643–1648. DOI: 10.1021/acs.joc.7b03045 Fei, T.; Walker, J. A.; Vickerman, K. L.; Stanley, L. M.; Jarboe, D.; Wang, T. “Synthesis and characterization of soybean oil-based waxes and their application as paraffin substitute for corrugated coating” Ind. Eng. Chem. Res. 2018, 56, 16371–16375.DOI: 10.1016/j.jiec.2017.09.015 Li, X.; Zhang, B.; Tang, L.; Tian, W. G.; Qi, S.; Volkov, A.; Pei, Y.; Qi, Z.; Tsung, C.; Stanley, L. M.; Huang, W“Cooperative Multifunctional Catalysts for Nitrone Synthesis: Platinum Nanoclusters in Amine‐Functionalized Metal–Organic Frameworks”Angew. Chem. Int. Ed. 2017, 58, 113–122. DOI: 10.1002/anie.201710164 Vickerman, K. L.; Stanley, L. M. “Catalytic, Enantioselective Synthesis of Polycyclic Nitrogen, Oxygen, and Sulfur Heterocycles via Rh-Catalyzed Alkene Hydroacylation” Org. Lett. 2017, 19, 5054–5057. DOI: 10.1021/acs.orglett.7b02230 Kadam, A. A.; Ellern, A.; Stanley, L. M. “Enantioselective, Palladium-Catalyzed Conjugate Additions of Arylboronic Acids to Form Bis-benzylic Quaternary Stereocenters” Org. Lett. 2017, 15, 4062–4065. DOI: 10.1021/acs.orglett.7b01825 Walker, J. A.; Vickerman, K. L.; Humke, J. N.; Stanley, L. M. “Ni-Catalyzed Alkene Carboacylation via Amide C–N Bond Activation” J. Am. Chem. Soc. 2017, 30, 10228–10231. DOI: 10.1021/jacs.7b06191 Metz, T. L.; Evans, J.; Stanley, L. M. “Catalytic Conjugate Addition of Electron-Rich Heteroarenes to ß,ß-Disubstituted Enones”Org Lett. 2017, 13, 3442-3445. DOI: 10.1021/acs.orglett.7b01402 Gerten, A. L.; Stanley, L. M. “Palladium-catalyzed conjugate addition of arylboronic acids to 2-substituted chromones in aqueous media” Tetrahedron Lett. 2016, 49, 5460-5463. DOI: 10.1016/j.tetlet.2016.10.084 Walker, J. A.; Stanley, L. M. “N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles” Org. Biomol. Chem. 2016, 42, 9981-9984. DOI: 10.1039/C6OB01956K Gao, M.; Cao, M.; Suastegui, M.; Walker, J. A.; Rodriguez-Quiroz, N.; Wu, Y.; Tribby, D.; Okerlund, A.; Stanley, L. M.; Shanks, J. V.; Shao, Z. “Innovating a Nonconventional Yeast Platform for Producing Shikimate as the Building Block of High-Value Aromatics” ACS Synth. Biol. 2017, 6, 29-38. DOI: 10.1021/acssynbio.6b00132 Johnson, K. F.; Schneider, E. A.; Schumacher, B. P.; Ellern, A.; Scanlon, J. D.; Stanley, L. M. “Rhodium-Catalyzed, Enantioselective Intramolecular Hydroacylation of Trisubstituted Alkenes” Chem. Eur. J. 2016, 44, 15619–15623.DOI: 10.1002/chem.201603880 Li, X.; Van Zeeland, R.; Maligal-Ganesh, R. V.; Pei, Y.; Power, G.; Stanley, L. M.; Huang, W. “Impact of Linker Engineering on the Catalytic Activity of Metal-Organic Frameworks Containing Pd(II)-Bipydridine Complexes” ACS Catal. 2016, 6, 6324-6328.DOI: 10.1021/acscatal.6b01753 Ghosh, A.; Bainbridge, D. T.; Stanley, L. M. “Enantioselective Model Synthesis and Progress toward the Putative Structure of Yuremamine” J. Org. Chem. 2016, 81, 7945-7951. DOI: 10.1021/acs.joc.6b01730 Ghosh, A.; Walker Jr., J. A.; Ellern, A.; Stanley, L. M. “Coupling Catalytic Alkene Hydroacylation and α-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Sterocenters” ACS Catal. 2016, 6, 2673-2680.DOI: 10.1021/acscatal.6b00365 Van Zeeland, R.; Li, X.; Huang, W.; Stanley, L. M. “MOF-253-Pd(OAc)2: A Recyclable MOF for Transition-Metal Catalysis in Water” RSC Adv. 2016, 6, 56330-56334. DOI: 10.1039/C6RA12746K