Publications

  • Janis Louie, John E. Gibby, Marc V. Farnworth, and Thomas N. Tekavec "Efficient Nickel-Catalyzed [2+2+2] Cycloaddition of CO2 and Diynes" J. Am. Chem. Soc., 2002, 124 (25), 15188-15189. Published, 11/2002.
  • H. A. Duong, T. N. Tekavec, A. M. Arif, J. Louie “Reversible Carboxylations of N-Heterocyclic Carbenes” Chem. Comm. 2004, 1, 112-113. Published, 02/2004.
  • G. Zuo, J. Louie “Highly Active Nickel Catalysts for the Isomerization of Unactivated Vinyl Cyclopropanes to Cyclopentenes” Angew. Chem. Int. Ed. 2004, 43, 2277-2279. Published, 04/2004.
  • T. N. Tekavec, A. M. Arif, J. Louie “Regioselectivity in Nickel-Catalyzed Cycloadditions of CO2 and Diynes” Tetrahedron 2004, 60, 7431-7437. Published, 05/2004.
  • M. V. Farnworth, M. J. Cross, J. Louie “Rhodium-Catalyzed Addition of Alcohols to Terminal Enones” Tetrahedron Lett. 2004, 45, 7441-7443. Published, 05/2004.
  • Hung A. Duong, Michael J. Cross, and Janis Louie "Nickel-Catalyzed Cycloaddition of Alkynes and Isocyanates" J. Am. Chem. Soc., 2004, 126 (37), pp 11438–11439. Published, 08/25/2004.
  • Hung A. Duong, Michael J. Cross, and Janis Louie "N-Heterocyclic Carbenes as Highly Efficient Catalysts for the Cyclotrimerization of Isocyanates" Org. Lett., 2004, 6 (25), pp 4679–4681. Published, 11/2004.
  • Michael M. McCormick, Hung A. Duong, Gang Zuo, and Janis Louie "A Nickel-Catalyzed Route to Pyridines" J. Am. Chem. Soc., 2005, 127 (14), pp 5030–5031. Published, 03/2005.
  • Gang Zuo and Janis Louie "Selectivity in Nickel-Catalyzed Rearrangements of Cyclopropylen-ynes" J. Am. Chem. Soc., 2005, 127 (16), pp 5798–5799. Published, 04/2005.
  • H. A. Duong, J. Louie “Regioselectivity in Ni/Phosphine Catalyzed Cycloadditions of Alkynes and Isocyanates” J. Organomet. Chem. 2005, 690, 5098-5104. Published, 06/2005.
  • Thomas N. Tekevac and Janis Louie "Nickel-Catalyzed Cycloaddition of Unsaturated Hydrocarbons and Carbonyl Compounds" Org. Lett., 2005, 7 (18), pp 4037–4039. Published, 07/2005.
  • H. A. Duong, J. Louie “A Nickel-Catalyzed Cycloaddition of Alkynes and Isocyanates that Affords Pyrimidine-diones” Tetrahedron 2006, 62, 7547-7551. Published, 03/2006.
  • T. N. Tekavec, G. Zuo, K. Simon, J. Louie “An In Situ Ni Catalyst for Cycloaddition Reactions” J. Org. Chem. 2006, 71, 5834-5836. Published, 06/2006.
  • P. R. Chopade, J. Louie “[2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes” Adv. Synth. Catal. 2006, 348, 2307-2327. Published, 08/2006.
  • Thomas N. Tekavec and Janis Louie "Nickel-Catalyzed Cycloadditions of Unsaturated Hydrocarbons, Aldehydes, and Ketones" J. Org. Chem., 2008, 73 (7), pp 2641–2648. Published, 03/05/2008.
  • T. N. Tekavec, J. Louie “Nickel-Catalyzed Cycloisomerization of Enynes: Mechanistic Evidence for Catalyst Generation via C-H Activation of Carbene Ligands” Tetrahedron 2008, 64, 6870-6875. Published, 04/2008.
  • K. Zhang, P. R. Chopade, J. Louie “Coupling of Vinyl Aziridines and Isocyanates” Tetrahedron Lett. 2008, 49, 4306-4309. Published, 05/2008.
  • G. Zuo, K. Zhang, J. Louie “Nickel Catalyzed Reactions of Vinyl Aziridines and Aziridinylen-ynes” Tetrahedron Lett. 2008, 49, 6797-6799. Published, 05/2008.
  • Brendan R. D’Souza and Janis Louie "Nickel-Catalyzed Cycloadditive Couplings of Enynes and Isocyanates" Org. Lett., 2009, 11 (18), pp 4168–4171. Published, 08/2009.
  • J. Ogle, N. Lahiri, C. Jaye, J. Tassone,, D. A. Fischer, J. Louie & L. Whittaker-Brooks (2020). Semiconducting to metallic electronic landscapes in defects controlled two-dimensional -d conjugated coordination polymer thin films. Adv. Functionalists. Mater. 2006920. Published, 09/2020.
  • R. Tsuchikawa, N. Lotfizadeh, N. Lahiri, S. Liu, M. Lach, J. Louie & V. V. Deshpande (2020). Unique Thermoelectric Properties Induced by Intrinsic Nanostructuring and Extrinsic Polycrystallinity in a 2D Metal-Organic Framework. Phys. Status Solidi. 437. Published, 04/2020.
  • A. L. Clevenger, R. M. Stolley, J. Aderibigbe & J. Louie (2020). Nickel and Bidentate Phosphines: Structure-Activity Relationships for Catalyst Formation. (pp. 6124-6196). Vol. 120. Chem. Rev. Published, 02/2020.
  • J. Renner & A. Thakur, P. M. Rutz, J. L. Evangelista, P. Kumar, M. B. Prater, R. M. Stolley, J. Louie (2020). Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4+2) Cyclization. Organic Letters. Vol. 22, 924-928. Published, 01/13/2020.
    https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9...
  • S. Datta & M. L. Saha, N. Lahiri, G. Yu, J. Louie, P. J. Stang (2018). Hierarchichal Self-Assembly of a Water Soluble Organoplatinum(II) Metallacycle into Well-Defined Nanostructures. Organic Letters. Vol. 20, 7020-7023. Published, 11/16/2018.
  • A. L. Clevenger & R. M. Stolley, N. D. Staudaher, N. Al, A. Rheingold, R. T. Vanderlinden, J. Louie (2018). A Comprehensive Study of the Reactions Between Chelating Phosphines and Ni(COD)2. Organometallics. Vol. 37, 3259-3268. Published, 10/08/2018.
  • S. Felten & S. F. Marshall, A. J. Groom,† R. T. Vanderlinden, R. M. Stolley, J. Louie (2018). Electronic Effect of Ligands on the Stability of Nickel-Ketene Complexes. Organometallics. Vol. 37, 3750-3755. Published, 10/2018.
  • N. Al & R. M. Stolley, N. D. Staudaher, R. T. Vanderlinden, J. Louie (2018). Electronic Effect of Ligands on the Stability of Nickel-Ketene Complexes. Organometallics. Vol. 37, 3750-3755. Published, 10/2018.
  • S. Datta & S. K. Misra, M. L. Saha, N. Lahiri, J. Louie, D. Pan, P. J. Stang (2018). Orthogonal Self-Assembly of an Organoplatinum(II) Metallacycle and Cucurbit[8]uril That Delivers Curcumin to Cancer Cells. PNAS. Vol. 115, 8087-8092. Published, 08/07/2018.
  • N. A. Spahn & M. H. Nguyen, J. Renner, J. Louie (2017). A Regioselective Iron-Catalyzed [2+2+2] Cycloaddition Reaction Forming 4,6-Disubstituted-2-Aminopyridines from Terminal Alkynes and Cyanamides. The Journal of Organic Chemistry. Vol. 82, 234-242. Published, 01/06/2017.
  • N. Lahari & N. Lotfizadeh, R. Tsuchikawa, V. V. Deshpande, J. Louie (2017). Hexaminobenzene as a Building Block for a Family of 2D Coordination Polymers. Journal of the American Chemical Society. Vol. 139, 19-22. Published, 01/2017.
  • N. D. Staudaher & A. M. Arif, J. Louie (2016). Synergy Between Experimental and Computational Chemistry Reveals the Mechanism of Decomposition of Nickel-Ketene Complexes. Journal of the American Chemical Society. Vol. 138, 14083-14091. Published, 10/2016.
  • N. D. Staudaher & J. Lovelace, M. P. Johnson, J. Louie (2016). Preparation of Aryl Alkyl Ketenes. Organic Syntheses. Vol. 94, 1-15. Published, 01/2016.
  • A. Thakur & J. Evangelista, J. Louie (2015). An in situ Ni-Catalyzed Approach to Substituted Piperidones. The Journal for Organic Chemistry. Vol. 80, 9951-9958. Published, 10/16/2015.
  • Y. Zhong & N. A. Spahn, R. M. Stolley, M. H. Nguyen, J. Louie (2015). 3,5-Disubstituted-2-Aminopyridines via Nicatalyzed Cycloaddition of Terminal Alkynes and Cyanamides. Synlett. Vol. 26, 307-312. Published, 09/2015.
  • A. Thakur & J.Louie (2015). Advances in nickel-catalyzed cycloaddition reactions to construct carbocycles and heterocycles. ACS Accounts of Chemical Research. Vol. 48, 2534-2365. Published, 08/18/2015.
    https://www.ncbi.nlm.nih.gov/pubmed/26200651
  • 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.. Published, 11/21/2014.
  • 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.. Published, 10/23/2014.
  • 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. Published, 09/23/2013.
  • 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.. Published, 08/28/2013.
  • 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. Published, 06/12/2013.
  • R. M. Stolley, J. Louie “The Organometallic Chemistry of Ni (update)” in Science of Synthesis; Plietker, B., ed.; Houben-Weyl: 2012. Published, 08/2012.
  • 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. Published, 06/2012.
  • 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. Published, 05/2012.
  • 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. Published, 04/2012.
  • 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. Published, 03/2012.
  • R. M. Stolley, W. X. Guo,† J. Louie “Palladium-Catalyzed Cross-Coupling of Cyanamides” Org. Lett. 2012, 14, 322-325. Published, 01/2012.
  • A. Thakur, K. Zhang, J. Louie “Suzuki-Miyaura Coupling if Hetero-aryl Boronic Acids and Vinyl Chlorides” Chem. Comm. 2012, 48, p203-205. Published, 11/2011.
  • 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. Published, 08/2011.
  • P. Kumar, J. Louie “Double the Fun: Nickel-Catalyzed Cycloaddition via Two Sequential C-H Activations” Angew. Chem. Int. Ed. 2011, 50, 10768-10769. Published, 08/2011.
  • 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. Published, 07/2011.
  • R. M. Stolley, M. T. Maczka, J. Louie “Nickel-Catalyzed Cycloaddition of Diynes and Cyanamides” 2011, 13, 3815-3824. Published, 03/2011.
  • 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. Published, 03/2011.
  • B. R. D’Souza, T. K. Lane, J. Louie “Iron Catalyzed Cycloaddition of Cyanoalkynes and Alkynes” Org. Lett. 2011, 13, 2936-2939. Published, 03/2011.
  • K. Zhang, M. Conda-Sheridan, S. Cooke, J. Louie “N-Heterocyclic Carbene Bound Ni(I)-Complexes and Their Roles in Catalysis” Organometallics 2011, 30, 2546-2552. Published, 03/2011.
  • K. Zhang, J. Louie “A Rhodium-Catalyzed Decarboxylative Cycloaddition Route to Substituted Anilines” J. Org. Chem. 2011, 76, 4686-4691. Published, 02/2011.
  • Selina C. Wang, Dawn M. Troast, Martin Conda-Sheridan, Gang Zuo, Donna LaGarde, Janis Louie and Dean J. Tantillo "Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement" J. Org. Chem., 2009, 74 (20), pp 7822–7833. Published, 09/2009.
  • Bret R. Van Ausdall, Jeremy L. Glass, Kelly M. Wiggins, Atta M. Aarif and Janis Louie "A Systematic Investigation of Factors Influencing the Decarboxylation of Imidazolium Carboxylates" J. Org. Chem., 2009, 74 (20), pp 7935–7942. Published, 09/2009.

Research Statement

The development of metal-mediated reactions has greatly expanded the synthesis of small molecules and polymeric materials. These complexes possess the profound ability to permit transformations that are otherwise energetically prohibited. Toward this end, our group hybridizes classical synthetic chemistry with state-of-the-art instrumentation to discover new metal-mediated reactions. Efforts focus on reaction optimization, mechanism elucidation, and constructing small and large molecules rich in structure and function.

Presentations

  • Indianapolis 246th National ACS Meeting. Invited Talk/Keynote, Presented, 09/06/2013.
  • Organometallic Gordon Conference. Invited Talk/Keynote, Presented, 08/08/2013.
  • (27) A. Thakur, J. Louie “Nickel Catalyzed Cycloaddition of 1,3-Dienes with 3-Azetidinones & 3-Oxetanones via C(sp2)-C(sp3) Bond Activation” Poster Presentation presented at Heterocycles Gordon Conference (2013). Contributed Talk, Presented, 03/02/2013.
  • Winter Conference on Medicinal and Bioorganic Chemistry (WCMBC): Frontiers in Synthesis Symposium . Invited Talk/Keynote, Presented, 01/20/2013.
  • Denver ACS Meeting. Invited Talk/Keynote, Accepted, 08/31/2011.

Research Groups

  • Ashish Thakur, Graduate Student. 03/2010 - present.
  • Jorge de Freitas, Graduate Student. 03/2009 - present.
  • Timothy K. Lane, Graduate Student. 03/2009 - 01/2014.
  • Ryan M. Stolley, Graduate Student. 03/2009 - 07/2013.
  • David R. Thomas, Graduate Student. 12/2007 - present.
  • Puneet Kumar, Graduate Student. 05/2007 - present.
  • Brendan D'Souza, Graduate Student. 01/2007 - present.
  • Kainan Zhang, Graduate Student. 11/2006 - 02/2011.
  • Bret Van Ausdall, Graduate Student. 03/2006 - present.