ORGANIC, INORGANIC, AND POLYMER CHEMISTRY
Professor and Henry Eyring Fellow
B.S. University of California, Los Angeles 1993
Ph.D. Yale University 1998
NIH Postdoctoral Fellow,
California Institute of Technology 1998-2001
Activities & Awards
- Henry Erying Assistant Professorship 2004
- NSF Faculty Early CAREER Development Award, 2004-2009
- ACS/Dreyfus PROGRESS “Rising Stars” Lectureship, 2005-2006
- Camille and Henry Dreyfus Teacher-Scholar Award, 2005-2010
- Alfred P. Sloan Award 2006
- CS Arthur C. Cope Scholar Award 2007
- Fellow of the American Association for the Advancement of Science, 2012
- Kavli Foundation Fellow, 2012
- Sigma Chi Beta Epsilon Chapter Teacher Appreciation Award, 2015
The central theme of our research is the discovery, development, and utilization of transition metal catalyzed reactions to overcome obstacles in traditional synthetic approaches. More specifically, we are interested in using metals to first elevate the reactivity of chemically inert reagents and then to exploit that heightened reactivity toward the construction of useful substrates. Ultimately, our hope is to provide synthetic chemists with a convenient and abbreviated approach to molecules rich with structural and/or functional diversity. Efforts are divided into catalyst discovery and optimization, mechanism elucidation, and application toward the construction of small molecules.
An attractive method for the rapid construction of the heterocyclic core of numerous biologically active pharmacophores is the cycloaddition or rearrangement of unsaturated substrates. Unfortunately, such cycloadditions are often not thermally allowed and existing alternatives show poor functional group compatibility. Thus, considerable effort has been focused on developing transition metal catalysts that mediate such transformations. Ultimately, reactions that require prohibitively harsh conditions (high temperatures, high pressures) may become practical (room temperature, atmospheric pressures) when a transition metal catalyst is employed. We believe cycloadditions are particularly attractive because they: 1) represent an ideal, atom-efficient entry to ring systems, 2) require only simple, readily available starting materials, 3) are functional group tolerant, and, most importantly, 4) could provide a wide assortment of heterocycles. As such, we have built a research program centered around the development of a general Ni- and Fe-based cycloaddition catalyst system.
In addition, the unsolved problem of CO2 activation continues to inspire us and has prompted another facet of our research program: metal-catalyzed CO2 activation reactions. As with our Ni-catalyzed cycloaddition chemistry, we seek to answer underlying, fundamental questions of what factors are important in reactions involving M-CO2 complexes.
- N. Lahari, R. Tsuchikawa, N. Lotfizadeh, V. V. Deshpande, J. Louie “Hexaminobenzene as a Building Block for Metal-Organic Graphene Analogs” Nature Mater. 2016, to be submitted.
- N. A. Spahn, M. H. Nguyen, J. Renner, J. Louie “A Regioselective Iron-Catalyzed Cycloaddition Reaction Forming 2-Aminopyridines from Terminal Alkynes and Cyanamides” J. Am. Chem. Soc. 2016, to be submitted.
- N.D. Staudaher, J. Lovelace, M. P. Johnson, J. Louie “Preparation of Aryl Alkyl Ketenes” Org. Synth. 2016, submitted.
- A. Thakur, J. Evangelista, J. Louie “An in situ Ni-Catalyzed Approach to Substituted Piperidones” J. Org. Chem. 2015, 80, 9951-9958.
- A. Thakur, J. Louie “Advances in Nickel-Catalyzed Cycloaddition Reactions To Construct Carbocycles and Heterocycles” Acc. Chem. Res. 2015, 48, 2534-2365; Invited Contribution to a Special Issue (Earth Abundant Metals in Homogeneous Catalysis).
- Y. Zhong, N. A. Spahn, R. M. Stolley, M. H. Nguyen, J. Louie “3,5-Disubstituted-2-Aminopyridines via Ni-catalyzed Cycloaddition of Terminal Alkynes and Cyanamides” Synlett 2015, 26, 307-312; Invited Contribution to a Special Issue (Cluster Report on Catalysis with Sustainable Metals).
- P. Kumar, A. Thakur, X. Hong, K. N. Houk, J. Louie “[Ni(NHC)]-catalyzed Cycloaddition of Diynes and Tropone: Apparent Enone Cycloaddition Involving an 8p Insertion” J. Am. Chem. Soc. 2014, 136, 17844-17851.
- N. D. Staudaher, R. M. Stolley, J. Louie “Synthesis, Mechanism of Formation, and Catalytic Activity of Xantphos Nickel p-Complexes” Chem. Commun. 2014, 50, 15577-15580.
- A. Thakur, M. E. Facer,† J. Louie “Nickel Catalyzed Cycloaddition of 1,3-Dienes with 3-Azetidinones and 3-Oxetanes” Angew. Chem. Int. Ed. 2013, 52, 12161-12165. PubMed PMID: 24573793; PubMed Central PMCID: PMC4113093.
- R. M. Stolley, H. A. Duong, J. Louie “Mechanistic Evaluation of the Ni(IPr)2-Catalyzed Cycloaddition of Alkynes and Nitriles to Afford Pyridines: Evidence for the Formation of a Key h1-Ni(IPr)2(RCN) Intermediate” Organometallics 2013, 32, 4952-4960. PubMed PMID: 25214702; PubMed Central PMCID: PMC4159214.
- T. K. Lane, M. H. Nguyen, N. Spahn, J. Louie “The Iron-Catalysed Construction of 2-Aminopyrimidines from Alkynenitriles and Cyanamides” Chem. Commun. 2013, 49, 7735-7737. PubMed PMID: 23877441; PubMed Central PMCID: PMC4144345.
- R. M. Stolley, H. A. Duong, D. R. Thomas, J. Louie “The Discovery of [Ni(IPr)RCN]2 Species and their Role as Cycloaddition Catalyts for the Formation of Pyridines” J. Am. Chem. Soc. 2012, 134, 15154-15162. PubMed PMID: 22917161; PubMed Central PMCID: PMC3480329.
- T. K. Lane, B. R. D’Souza, J. Louie “2-Aminopyridines from Iron-Catalyzed Cycloaddition of Diynes and Cyanamides” J. Org. Chem. 2012, 77, 7555-7563. PubMed PMID: 22845666; PubMed Central PMCID: PMC3480319.
- P. Kumar, K. Zhang, J. Louie “An Expeditious Route to Eight-Membered Heterocycles by Nickel-Catalyzed Cycloaddition: Low-Temperature Csp2-Csp3 Bond Cleavage” Angew. Chem. Int. Ed. 2012, 51, 8602-8606. PubMed PMID: 22806996; PubMed Central PMCID: PMC3557805.
- P. Kumar, J. Louie “A Single Step Approach to Highly Substituted Piperidines Via Ni-Catalyzed
β-Carbon Elimination” Org. Lett. 2012, 14, 2026-2029; Synfacts Highlight 2012, 8(7), 0715;
Synfacts Highlight 2012, 8(9), 0949. PubMed PMID: 22468962; PubMed Central PMCID: PMC4138124.
- R. M. Stolley, W. X. Guo,† J. Louie “Palladium-Catalyzed Cross-Coupling of Cyanamides” Org. Lett. 2012, 14, 322-325; C & E News December 19, 2011. PubMed PMID: 22142553; PubMed Central PMCID: PMC4113087.
- B. R. Van Ausdall, N. F. Pols,† V. A. Kincaid,† A. M. Aarif, J. Louie “NHC·CO2-bound MBPh4 Complexes (M = Li, Na) and their Relevance in Transcarboxylation Reactions” J. Org. Chem. 2011, 76, 8413-8420.
- P. Kumar, S. Prescher,† J. Louie “A Serendipitous Discovery of a Nickel-Catalyst for Cycloaddition of Diynes with Unactivated Nitriles” Angew. Chem. Int. Ed. 2011, 50, 10694-10698; Synfacts Highlight 2012, 8(1), 0018 DOI: 10.1055/s-0031-1289949. PubMed PMID: 21932226; PubMed Central PMCID: PMC3557808.
- R. M. Stolley, M. T. Maczka,† J. Louie “Nickel-Catalyzed Cycloaddition of Diynes and Cyanamides” Eur. J. Org. Chem. 2011, 20-21, 3815-3824; Invited Contribution to a Special Edition Honoring Women in Chemistry. PubMed PMID: 25346615; PubMed Central PMCID: PMC4208422.
- B. R. D’Souza, T. K. Lane, J. Louie “Iron Catalyzed Cycloaddition of Cyanoalkynes and Alkynes” Org. Lett. 2011, 13, 2936-2939. PubMed PMID: 21557582; PubMed Central PMCID: PMC3203642.
- P. Kumar, D. M. Troast, R. Cella, J. Louie “Ni-Catalyzed Ketene Cycloaddition: A System that Resists the Formation of Decarbonylation Side Products” J. Am. Chem. Soc. 2011, 133, 7719-7721; C & E News May 9, 2011. PubMed PMID: 21528904; PubMed Central PMCID: PMC3107595.
- T. N. Tekavec, J. Louie “Nickel-Catalyzed Cycloadditions of Unsaturated Hydrocarbons, Aldehydes, and Ketones” J. Org. Chem. 2008, 73, 2641-2648. PubMed PMID: 18318544; PubMed Central PMCID: PMC4144363.
- T. N. Tekavec, G. Zuo, K. Simon,† J. Louie “An In Situ Ni Catalyst for Cycloaddition Reactions” J. Org. Chem. 2006, 71, 5834-5836.
- G. Zuo, J. Louie “Selectivity in Nickel-Catalyzed Rearrangements of Cyclopropylen-ynes” J. Am. Chem. Soc. 2005, 127, 5798-5799.
- M. M. McCormick, H. A. Duong, G. Zuo, J. Louie “A Nickel-Catalyzed Route to Pyridines” J. Am. Chem. Soc. 2005, 127, 5030-5031.
- J. Louie, J. E. Gibby,† M. V. Farnworth,† T. N. Tekavec “Efficient Nickel-Catalyzed [2+2+2] Cycloaddition of CO2 and Diynes” J. Am. Chem. Soc. 2002, 124, 15188-15189; 2004, 8590 (addition/correction).