Publications

  • P. Kumar (date unknown). P. Kumar, J. Louie “Nickel-Mediated Cycloaddition (Chapter 2.3 in Chapter 2: [2+2+2] and [2+2+1] Cycloaddition) in Transition-Metal-Mediated Aromatic Ring Construction, Tanaka, K., ed.; John Wiley & Sons Ltd.: Chichester, 2012. Accepted, .
  • R. M. Stolley (date unknown). R. M. Stolley, J. Louie “The Organometallic Chemistry of Ni (update)” in Science of Synthesis; Plietker, B., ed.; Houben-Weyl: 2012. Accepted, .
  • Janis Louie (date unknown). Origins of Regio- and Chemoselective Iron-Catalyzed [2+2+2] Cycloaddition Syntheses of 4,6-Disubstituted 2-Aminopyridines. ACS Catalysis. Vol. 11, 14677–14687. Accepted, .
  • P. Kumar (date unknown). 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. Accepted, .
  • S. Datta (date unknown). Hierarchichal Self-Assembly of a Water Soluble Organoplatinum(II) Metallacycle into Well-Defined Nanostructures. Organic Letters. Vol. 20, 7020-7023. Accepted, .
  • Ashish Thakur (date unknown). A. Thakur, K. Zhang, J. Louie “Suzuki-Miyaura Coupling if Hetero-aryl Boronic Acids and Vinyl Chlorides” Chem. Comm. 2012, 48, p203-205. Accepted, .
  • (date unknown). 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. Accepted, .
  • (date unknown). 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. Accepted, .
  • N. D. Staudaher (date unknown). 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. Accepted, .
  • A. Thakur (date unknown). An in situ Ni-Catalyzed Approach to Substituted Piperidones. The Journal for Organic Chemistry. Vol. 80, 9951-9958. Accepted, .
  • A. L. Clevenger (date unknown). A Comprehensive Study of the Reactions Between Chelating Phosphines and Ni(COD)2. Organometallics. Vol. 37, 3259-3268. Accepted, .
  • N. Al (date unknown). Electronic Effect of Ligands on the Stability of Nickel-Ketene Complexes. Organometallics. Vol. 37, 3750-3755. Accepted, .
  • S. Felten (date unknown). Electronic Effect of Ligands on the Stability of Nickel-Ketene Complexes. Organometallics. Vol. 37, 3750-3755. Accepted, .
  • N. D. Staudaher (date unknown). 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. Accepted, .
  • A. Thakur (date unknown). 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. Accepted, .
  • J. Ogle (date unknown). Semiconducting to metallic electronic landscapes in defects controlled two-dimensional -d conjugated coordination polymer thin films. Adv. Functionalists. Mater. 2006920. Accepted, .
  • Y. Zhong (date unknown). 3,5-Disubstituted-2-Aminopyridines via Nicatalyzed Cycloaddition of Terminal Alkynes and Cyanamides. Synlett. Vol. 26, 307-312. Accepted, .
  • (date unknown). 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. Accepted, .
  • (date unknown). 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. Accepted, .
  • R.M. Stolley (date unknown). 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. Accepted, .
  • (date unknown). 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. Accepted, .
  • A. Thakur (date unknown). Advances in nickel-catalyzed cycloaddition reactions to construct carbocycles and heterocycles. ACS Accounts of Chemical Research. Vol. 48, 2534-2365. Accepted, .
  • S. Datta (date unknown). Orthogonal Self-Assembly of an Organoplatinum(II) Metallacycle and Cucurbit[8]uril That Delivers Curcumin to Cancer Cells. PNAS. Vol. 115, 8087-8092. Accepted, .
  • Puneet Kumar (date unknown). P. Kumar, J. Louie “Double the Fun: Nickel-Catalyzed Cycloaddition via Two Sequential C-H Activations” Angew. Chem. Int. Ed. 2011, 50, 10768-10769. Accepted, .
  • Puneet Kumar (date unknown). 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. Accepted, .
  • (date unknown). Brendan R. D’Souza and Janis Louie "Nickel-Catalyzed Cycloadditive Couplings of Enynes and Isocyanates" Org. Lett., 2009, 11 (18), pp 4168–4171. Accepted, .
  • (date unknown). P. R. Chopade, J. Louie “[2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes” Adv. Synth. Catal. 2006, 348, 2307-2327. Accepted, .
  • Bret Van Ausdall (date unknown). 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. Accepted, .
  • (date unknown). Thomas N. Tekevac and Janis Louie "Nickel-Catalyzed Cycloaddition of Unsaturated Hydrocarbons and Carbonyl Compounds" Org. Lett., 2005, 7 (18), pp 4037–4039. Accepted, .
  • T.K. Lane (date unknown). 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. Accepted, .
  • R. M. Stolley (date unknown). 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. Accepted, .
  • (date unknown). T. N. Tekavec, G. Zuo, K. Simon, J. Louie “An In Situ Ni Catalyst for Cycloaddition Reactions” J. Org. Chem. 2006, 71, 5834-5836. Accepted, .
  • (date unknown). H. A. Duong, J. Louie “Regioselectivity in Ni/Phosphine Catalyzed Cycloadditions of Alkynes and Isocyanates” J. Organomet. Chem. 2005, 690, 5098-5104. Accepted, .
  • T. K. Lane (date unknown). 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. Accepted, .
  • (date unknown). K. Zhang, P. R. Chopade, J. Louie “Coupling of Vinyl Aziridines and Isocyanates” Tetrahedron Lett. 2008, 49, 4306-4309. Accepted, .
  • (date unknown). G. Zuo, K. Zhang, J. Louie “Nickel Catalyzed Reactions of Vinyl Aziridines and Aziridinylen-ynes” Tetrahedron Lett. 2008, 49, 6797-6799. Accepted, .
  • (date unknown). T. N. Tekavec, A. M. Arif, J. Louie “Regioselectivity in Nickel-Catalyzed Cycloadditions of CO2 and Diynes” Tetrahedron 2004, 60, 7431-7437. Accepted, .
  • (date unknown). M. V. Farnworth, M. J. Cross, J. Louie “Rhodium-Catalyzed Addition of Alcohols to Terminal Enones” Tetrahedron Lett. 2004, 45, 7441-7443. Accepted, .
  • R. Tsuchikawa (date unknown). Unique Thermoelectric Properties Induced by Intrinsic Nanostructuring and Extrinsic Polycrystallinity in a 2D Metal-Organic Framework. Phys. Status Solidi. 437. Accepted, .
  • P. Kumar (date unknown). 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. Accepted, .
  • (date unknown). 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. Accepted, .
  • (date unknown). Gang Zuo and Janis Louie "Selectivity in Nickel-Catalyzed Rearrangements of Cyclopropylen-ynes" J. Am. Chem. Soc., 2005, 127 (16), pp 5798–5799. Accepted, .
  • (date unknown). 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. Accepted, .
  • (date unknown). Thomas N. Tekavec and Janis Louie "Nickel-Catalyzed Cycloadditions of Unsaturated Hydrocarbons, Aldehydes, and Ketones" J. Org. Chem., 2008, 73 (7), pp 2641–2648. Accepted, .
  • P. Kumar (date unknown). 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. Accepted, .
  • R. M. Stolley (date unknown). R. M. Stolley, M. T. Maczka, J. Louie “Nickel-Catalyzed Cycloaddition of Diynes and Cyanamides” 2011, 13, 3815-3824. Accepted, .
  • Puneet Kumar (date unknown). 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. Accepted, .
  • Brendan R. D'Souza (date unknown). B. R. D’Souza, T. K. Lane, J. Louie “Iron Catalyzed Cycloaddition of Cyanoalkynes and Alkynes” Org. Lett. 2011, 13, 2936-2939. Accepted, .
  • Kainan Zhang (date unknown). 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. Accepted, .
  • (date unknown). H. A. Duong, J. Louie “A Nickel-Catalyzed Cycloaddition of Alkynes and Isocyanates that Affords Pyrimidine-diones” Tetrahedron 2006, 62, 7547-7551. Accepted, .
  • (date unknown). 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. Accepted, .
  • Kainan Zhang (date unknown). K. Zhang, J. Louie “A Rhodium-Catalyzed Decarboxylative Cycloaddition Route to Substituted Anilines” J. Org. Chem. 2011, 76, 4686-4691. Accepted, .
  • (date unknown). H. A. Duong, T. N. Tekavec, A. M. Arif, J. Louie “Reversible Carboxylations of N-Heterocyclic Carbenes” Chem. Comm. 2004, 1, 112-113. Accepted, .
  • J. Renner (date unknown). Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4+2) Cyclization. Organic Letters. Vol. 22, 924-928. Accepted, .
  • N. A. Spahn (date unknown). 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. Accepted, .
  • N. Lahari (date unknown). Hexaminobenzene as a Building Block for a Family of 2D Coordination Polymers. Journal of the American Chemical Society. Vol. 139, 19-22. Accepted, .
  • N. D. Staudaher (date unknown). Preparation of Aryl Alkyl Ketenes. Organic Syntheses. Vol. 94, 1-15. Accepted, .
  • Ryan Stolley (date unknown). R. M. Stolley, W. X. Guo,† J. Louie “Palladium-Catalyzed Cross-Coupling of Cyanamides” Org. Lett. 2012, 14, 322-325. Accepted, .
  • A. L. Clevenger (date unknown). Nickel and Bidentate Phosphines: Structure-Activity Relationships for Catalyst Formation. (pp. 6124-6196). Vol. 120. Chem. Rev. Accepted, .

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

  • (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, 2013.
  • Indianapolis 246th National ACS Meeting. , Presented, 2013.
  • Organometallic Gordon Conference. , Presented, 2013.
  • Winter Conference on Medicinal and Bioorganic Chemistry (WCMBC): Frontiers in Synthesis Symposium. , Presented, 2013.
  • Denver ACS Meeting. , Accepted, 2011.

Research Groups

  • Ashish Thakur, . 2010 - present.
  • Jorge de Freitas, . 2009 - present.
  • Ryan M. Stolley, . 2009 - 2013.
  • Timothy K. Lane, . 2009 - 2014.
  • David R. Thomas, . 2007 - present.
  • Puneet Kumar, . 2007 - present.
  • Brendan D'Souza, . 2007 - present.
  • Kainan Zhang, . 2006 - 2011.
  • Bret Van Ausdall, . 2006 - present.