heterocycles

Continuous Flow Enables Metallaphotoredox Catalysis in a Medicinal Chemistry Setting: Accelerated Optimization and Library Execution of a Reductive Coupling between Benzylic Chlorides and Aryl Bromides

Merck
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  • Z.G. Brill, C.B. Ritts, U.F. Mansoor, and N. Sciammetta, "Continuous Flow Enables Metallaphotoredox Catalysis in a Medicinal Chemistry Setting: Accelerated Optimization and Library Execution of a Reductive Coupling between Benzylic Chlorides and Aryl Bromides", Organic Letters, vol. 22, pp. 410-416, 2019. http://dx.doi.org/10.1021/acs.orglett.9b04117
  • Nitroacetic Esters in the Regioselective Synthesis of Isoxazole-3,5-dicarboxylic Acid Derivatives

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  • A.Y. Smirnov, E.R. Zaitseva, O.A. Belozerova, R.S. Alekseyev, N.S. Baleeva, M.B. Zagudaylova, A.A. Mikhaylov, and M.S. Baranov, "Nitroacetic Esters in the Regioselective Synthesis of Isoxazole-3,5-dicarboxylic Acid Derivatives", The Journal of Organic Chemistry, vol. 84, pp. 15417-15428, 2019. http://dx.doi.org/10.1021/acs.joc.9b02427
  • Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles

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  • B.A. Chalyk, A. Khutorianskyi, A. Lysenko, Y. Fil, Y.O. Kuchkovska, K.S. Gavrilenko, I. Bakanovych, Y.S. Moroz, A.O. Gorlova, and O.O. Grygorenko, "Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles", The Journal of Organic Chemistry, vol. 84, pp. 15212-15225, 2019. http://dx.doi.org/10.1021/acs.joc.9b02258
  • Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes

    Enamine chemists reported a comprehensive study of regioselective [3 + 2] cycloaddition reactions – an efficient approach towards 3,5-disubstituted isoxazole building blocks bearing mono-, di- or trifluoromethyl substituents. More than 100 derivatives were obtained on up to 130 g scale, and multigram quantities of representative examples are available from EnamineStore at the isoxazole library
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  • B.A. Chalyk, K.V. Hrebeniuk, Y.V. Fil, K.S. Gavrilenko, A.B. Rozhenko, B.V. Vashchenko, O.V. Borysov, A.V. Biitseva, P.S. Lebed, I. Bakanovych, Y.S. Moroz, and O.O. Grygorenko, "Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes", The Journal of Organic Chemistry, vol. 84, pp. 15877-15899, 2019. http://dx.doi.org/10.1021/acs.joc.9b02264
  • Preparation of 2-(2H-Tetrazol-2-yl)benzoic Acids via Regioselective Cu(I) Catalyzed N2 Arylation of Tetrazole

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  • Z.J. Song, P. Maligres, C. Molinaro, G. Humphrey, J. Fritzen, J. Wilson, and Y. Chen, "Preparation of 2-(2H-Tetrazol-2-yl)benzoic Acids via Regioselective Cu(I) Catalyzed N2 Arylation of Tetrazole", Organic Process Research & Development, vol. 23, pp. 2354-2361, 2019. http://dx.doi.org/10.1021/acs.oprd.9b00243
  • Late-Stage Diversification of Imidazole-Based Pharmaceuticals through Pd-Catalyzed Regioselective C–H Bond Arylations


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  • A. Benzai, X. Shi, F. Derridj, T. Roisnel, H. Doucet, and J. Soulé, "Late-Stage Diversification of Imidazole-Based Pharmaceuticals through Pd-Catalyzed Regioselective C–H Bond Arylations", The Journal of Organic Chemistry, vol. 84, pp. 13135-13143, 2019. http://dx.doi.org/10.1021/acs.joc.9b01469
  • Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines


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  • E. Duchamp, B.D. Simard, and S. Hanessian, "Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines", Organic Letters, vol. 21, pp. 6593-6596, 2019. http://dx.doi.org/10.1021/acs.orglett.9b01842
  • Data-Rich Experimentation Enables Palladium-Catalyzed Couplings of Piperidines and Five-Membered (Hetero)aromatic Electrophiles

    (Merck & Co.)

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  • A.C. Sather, and T.A. Martinot, "Data-Rich Experimentation Enables Palladium-Catalyzed Couplings of Piperidines and Five-Membered (Hetero)aromatic Electrophiles", Organic Process Research & Development, vol. 23, pp. 1725-1739, 2019. http://dx.doi.org/10.1021/acs.oprd.9b00233
  • Intramolecular Homolytic Substitution Enabled by Photoredox Catalysis: Sulfur, Phosphorus, and Silicon Heterocycle Synthesis from Aryl Halides


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  • A.F. Garrido-Castro, N. Salaverri, M.C. Maestro, and J. Alemán, "Intramolecular Homolytic Substitution Enabled by Photoredox Catalysis: Sulfur, Phosphorus, and Silicon Heterocycle Synthesis from Aryl Halides", Organic Letters, vol. 21, pp. 5295-5300, 2019. http://dx.doi.org/10.1021/acs.orglett.9b01911