Mechanochemistry

  • Molecular Recognition in Mechanochemistry: Insights from Solid-State NMR Spectroscopy
    C. Quaranta, I. d'Anciães Almeida Silva, S. Moos, E. Bartalucci, L. Hendrickx, B. M. D. Fahl, C. Pasqualini, F. Puccetti, M. Zobel, C. Bolm, T. Wiegand, Angew. Chem. Int. Ed. 2024, 63, e202410801.
    Also published as a preprint at ChemRxiv.

  • Diversification of NH-Aryl Sulfoximines through Iridium-Catalyzed ortho- and meta-Selective C–H Borylation
    P. van Bonn, S. Soerensen, N. Schmitz, C. Bolm, Adv. Synth. Catal. 2024, 366, 725–732.

  • Mechanochemical Mitsunobu Reactions
    M. T. J. Williams, L. Adarve Cardona, C. Bolm, Adv. Synth. Catal. 2024, 366, 2220–2225.

  • Synthesis of α-ketothioamides with elemental sulfur under solvent-free conditions in a mixer mill
    C. C. Sahu, S. Biswas, R. Hommelsheim, C. Bolm, RSC Mechanochem. 2024, 1, 38–42.

  • Mechanochemical Iron-Catalyzed Nitrene Transfer Reactions: Direct Synthesis of N-Acyl Sulfonimidamides from Sulfinamides and Dioxazolones
    S. Pan, F. F. Mulks, P. Wu, K. Rissanen, C. Bolm, Angew. Chem. Int. Ed. 2024, 63, e202316702.

  • Halogen bonding and mechanochemistry combined: synthesis, characterization, and application of N-iodosaccharin pyridine complexes
    C. Schumacher, K.-N. Truong, J. S. Ward, R. Puttreddy, A. Rajala, E. Lassila, C. Bolm, K. Rissanen, Org. Chem. Front. 2024, 11, 781–795.
    Also published as a preprint at ChemRxiv.

  • Rhodium(II)-Catalyzed N–H Insertions of Carbenes under Mechanochemical Conditions
    S. Biswas, C. Bolm, Org. Lett. 2024, 26, 1511–1516.

  • Advances in synthesis: general discussion
    A. Angerhofer, M. Baláž, V. Balema, A. M. Belenguer, R. G. Blair, E. Boldyreva, C. Bolm, L. Borchardt, A. B. Braunschweig, D. L. Browne, S. Craig, L. El Wenni, F. Emmerling, M. Ferguson, C. Fiore, T. Friščić, K. Fukushima, F. García, L. Gonnet, S. Grätz, R. A. Hernandez R., H. Ito, S. L. James, D. Karabiyikli, J. G. Kim, K. Kubota, F. Lamaty, G. I. Lampronti, J. Leitch, S. Lukin, J. Mack, L. Maini, S. Mohamed, A. Moores, K. Nagapudi, F. Puccetti, M. Tian, Q. Yu, Faraday Discuss. 2023, 241, 150–177.

  • Kinetics and basic understanding: general discussion
    A. Angerhofer, T. Auvray, V. Balema, M. Baláž, J. D. Batteas, R. G. Blair, E. Boldyreva, C. Bolm, L. Borchardt, T. H. Borchers, A. B. Braunschweig, D. L. Browne, R. W. Carpick, M. Ciaccia, S. Craig, F. Emmerling, M. Ferguson, C. Fiore, T. Friščić, S. Grätz, I. Halasz, E. Hamzehpoor, H. Ito, S. James, J. G. Kim, F. Lamaty, G. I. Lampronti, D. Laurencin, J. Leitch, E. Lu, S. Lukin, J. Mack, L. Maini, A. Martini, P. P. Mazzeo, A. A. L. Michalchuk, S. Mittelette, S. Mohamed, A. Moores, A. d. J. Mortera-Carbonell, K. Nagapudi, A. Niidu, F. Puccetti, M. Stahorský, L. Vugrin, Faraday Discuss. 2023, 241, 306–340.

  • Scale up and industrial implementation: general discussion
    M. Baláž, V. Balema, J. D. Batteas, R. G. Blair, C. Bolm, L. Borchardt, A. B. Braunschweig, S. L. Craig, F. Emmerling, M. Ferguson, T. Friščić, S. James, J. Leitch, J. Mack, S. Mohamed, K. Nagapudi, F. Puccetti, M. E. Rivas, Faraday Discuss. 2023, 241, 387–393.

  • Shear processes and polymer mechanochemistry: general discussion
    M. Baláž, V. Balema, R. G. Blair, E. Boldyreva, C. Bolm, A. B. Braunschweig, R. W. Carpick, S. L. Craig, F. Emmerling, J. P. Ewen, C. Fiore, T. Friščić, S. Grätz, I. Halasz, E. Hamzehpoor, H. Ito, J. G. Kim, G. I. Lampronti, D. Laurencin, J. Mack, L. Maini, P. P. Mazzeo, S. Mohamed, K. Nagapudi, A. Niidu, J. Vainauskas, C. Zuffa, Faraday Discuss. 2023, 241, 466–484.

  • Reshuffle Bonds by Ball Milling: A Mechanochemical Protocol for Charge-Accelerated Aza-Claisen Rearrangements
    C. Schumacher, L. Fritz, L. M. Hanek, V. Sidorin, D. Brüx, C. Bolm, Molecules 2023, 28, 807.

  • Disentangling the Effect of Pressure and Mixing on a Mechanochemical Bromination Reaction by Solid-state NMR Spectroscopy
    E. Bartalucci, C. Schumacher, L. Hendrickx, F. Puccetti, I. d'Anciães Almeida Silva, R. Dervişoğlu, R. Puttreddy, C. Bolm, T. Wiegand, Chem. Eur. J. 2023, 29, e202203466.

  • NMR in operando monitoring of mechanochemically accelerated sublimations
    F. Puccetti, T. Rinesch, S. Suljić, K. Rahimi, A. Herrmann, C. Bolm, Chem 2023, 9, 1318–1332.

  • Mechanochemical Oxidative Degradation of Thienopyridine Containing Drugs: Toward a Simple Tool for the Prediction of Drug Stability
    E. F. Krake, L. Backer, B. Andres, W. Baumann, N. Handler, H. Buschmann, U. Holzgrabe, C. Bolm, T. Beweries, ACS Cent. Sci. 2023, 9, 1150–1159.

  • Mechanochemical difluoromethylations of alcohols
    P. van Bonn, J. Ke, C. Weike, J. S. Ward, K. Rissanen, C. Bolm, CCS Chem. 2023, 5, 1737–1744.

  • Mechanochemical Synthesis of Stimuli Responsive Microgels
    C. Hu, P. van Bonn, D. E. Demco, C. Bolm, A. Pich, Angew. Chem. Int. Ed. 2023, 62, e202305783.

  • Opportunities and Challenges in Applying Solid-State NMR Spectroscopy in Organic Mechanochemistry
    I. d'Anciães Almeida Silva, E. Bartalucci, C. Bolm, T. Wiegand, Adv. Mater. 2023, 35, 2304092.
    Also published as a preprint at ChemRxiv.

  • Mechanochemical difluoromethylations of alcohols
    P. van Bonn, J. Ke, C. Weike, J. S. Ward, K. Rissanen, C. Bolm, CCS Chem. 2023, 5, 1737–1744.

  • Reshuffle Bonds by Ball Milling: A Mechanochemical Protocol for Charge-Accelerated Aza-Claisen Rearrangements
    C. Schumacher, L. Fritz, L. M. Hanek, V. Sidorin, D. Brüx, C. Bolm, Molecules 2023, 28, 807.

  • Electro-mechanochemical approach towards chloro sulfoximidations of allenes under solvent-free conditions in a ball mill
    M. M. Amer, R. Hommelsheim, C. Schumacher, D. Kong, C. Bolm, Faraday Discuss. 2023, 241, 79–90.

  • NMR in operando monitoring of mechanochemically accelerated sublimations
    F. Puccetti, T. Rinesch, S. Suljić, K. Rahimi, A. Herrmann, C. Bolm, Chem 2023, 9, 1318–1332.
    Also published as a preprint at ChemRxiv.

  • Disentangling the Effect of Pressure and Mixing on a Mechanochemical Bromination Reaction by Solid-state NMR Spectroscopy
    E. Bartalucci, C. Schumacher, L. Hendrickx, F. Puccetti, I. d'Anciães Almeida Silva, R. Dervişoğlu, R. Puttreddy, C. Bolm, T. Wiegand, Chem. Eur. J. 2023, 29, e202203466.

  • Iron-catalyzed Intramolecular Arene C(sp2)–H Amidations under Mechanochemical Conditions
    P. Shi, Y. Tu, D. Kong, P. Wu, D. Ma, C. Bolm, Angew. Chem. Int. Ed. 2022, 61, e202204874.
    Selected as Hot Paper.

  • Sulfonimidamides by Sequential Mechanochemical Chlorinations and Aminations of Sulfinamides
    S. Terhorst, T. Jansen, T. Langletz, C. Bolm, Org. Lett. 2022, 24, 4109–4113.

  • Mechanochemical Synthesis of Diarylethynes from Aryl Iodides and CaC2
    P. van Bonn, C. Bolm, Synlett 2022, 33, 893–897.

  • Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate
    V. S. Pfennig, R. C. Villella, J. Nikodemus, C. Bolm, Angew. Chem. Int. Ed. 2022, 61, e202116514.
    Selected as Hot Paper. Also published as a preprint at ChemRxiv.

  • Mechanistic Insights on the Mechanosynthesis of Phenytoin, a WHO Essential Medicine
    F. Puccetti, S. Lukin, K. Užarević, E. Colacino, I. Halasz, C. Bolm, J. G. Hernández, Chem. Eur. J. 2022, 28, e202104409.
    Also published as a preprint at ChemRxiv.

  • The Mechanochemical Synthesis and Activation of Carbon-Rich π-Conjugated Matarials
    M. Xuan, C. Schumacher, C. Bolm, R. Göstl, A. Herrmann, Adv. Sci. 2022, 9, 2105497.

  • Mechanochemical Palladium-Catalyzed Oxidative Esterification of Alcohols
    P. van Bonn, D. Dreßler, F. Weitenhagen, C. Bolm, ACS Sustainable Chem. Eng. 2022, 10, 1361–1366.

  • Mechanochemical Solvent-Free N-Sulfenylations of Sulfoximines and Sulfonimidamides
    D. Kong, D. Ma, P. Wu, C. Bolm, ACS Sustainable Chem. Eng. 2022, 10, 2863–2867.

  • Enabling Techniques for Organic Synthesis
    C. O. Kappe, J. Mack, C. Bolm, J. Org. Chem. 2021, 86, 14242–14244.

  • Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC
    C. Schumacher, C. Molitor, S. Smid, K.‐N. Truong, K. Rissanen, C. Bolm, J. Org. Chem. 2021, 86, 14213–14222.

  • Ball milling – a new concept for predicting degradation profiles in active pharmaceutical ingredients
    R. P. Kaiser, E. F. Krake, L. Backer, J. Urlaub, W. Baumann, N. Handler, H. Buschmann, T. Beweries, U. Holzgrabe, C. Bolm, Chem. Commun. 2021, 57, 11956–11959.

  • 2,3-Dihydro-1,2,6-thiadiazine 1-Oxides by Biginelli-Type Reactions with Sulfonimidamides under Mechanochemical Conditions
    F. Krauskopf, K.‐N. Truong, K. Rissanen, C. Bolm, Org. Lett. 2021, 23, 2699–2703.

  • N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines: synthesis, X-ray crystallography, and halogen bonding
    C. Schumacher, H. Fergen, R. Puttreddy, K.-N. Truong, T. Rinesch, K. Rissanen, C. Bolm, Org. Chem. Front. 2020, 7, 3896–3906.

  • Mechanochemical Synthesis of 1,2,6-Thiadiazine 1-Oxides from Sulfonimidamides and the Fluorescence Properties of the Products
    J.-H. Schöbel, W. Liang, D. Wöll, C. Bolm, J. Org. Chem. 2020, 85, 15760–15766.

  • The Use of Copper and Vanadium Mineral Ores in Catalyzed Mechanochemical Carbon–Carbon Bond Formations
    F. Puccetti, C. Schumacher, H. Wotruba, J. G. Hernández, C. Bolm, ACS Sustainable Chem. Eng. 2020, 8, 7262–7266. Also published as a preprint at ChemRxiv.

  • Electro‐Mechanochemical Atom Transfer Radical Cyclizations using Piezoelectric BaTiO3
    C. Schumacher, J. G. Hernández, C. Bolm, Angew. Chem. 2020, 132, 16499–16502; Angew. Chem. Int. Ed. 2020, 59, 16357–16360.

  • Direct Visualization of a Mechanochemically Induced Molecular Rearrangement
    K. J. Ardila-Fierro, S. Lukin, M. Etter, K. Užarević, I. Halasz, C. Bolm, J. G. Hernández, Angew. Chem. 2020, 132, 13560–13564; Angew. Chem. Int. Ed. 2020, 59, 13458–13462.

  • Mechanochemical Palladium‐Catalyzed Carbonylative Reactions Using Mo(CO)6
    P. van Bonn, C. Bolm, J. G. Hernández, Chem. Eur. J. 2020, 26, 2576–2580. Selected as Hot Paper.

  • Mechanosynthesis of Odd‐Numbered Tetraaryl[n]cumulenes
    K. J. Ardila-Fierro, C. Bolm, J. G. Hernández, Angew. Chem. 2019, 131, 13079–13083; Angew. Chem. Int. Ed. 2019, 58, 12945–12949.

  • Mechanochemical Copper‐Catalyzed Asymmetric Michael‐Type Friedel–Crafts Alkylation of Indoles with Arylidene Malonates
    P. Staleva, J. G. Hernández, C. Bolm, Chem. Eur. J. 2019, 25, 9202–9205.

  • Synthesis of acylglycerol derivatives by mechanochemistry
    K. J. Ardila-Fierro, A. Pich, M. Spehr, J. G. Hernández, C. Bolm, Beilstein J. Org. Chem. 2019, 15, 811–817.

  • Mechanochemistry of gaseous reactants
    C. Bolm, J. G. Hernández, Angew. Chem. 2019, 131, 3320–3335; Angew. Chem. Int. Ed. 2019, 58, 3285–3299.

  • Mechanochemical Rhodium(III)‐ and Gold(I)‐Catalyzed C–H Bond Alkynylations of Indoles under Solventless Conditions in Mixer Mills
    G. N. Hermann, M. T. Unruh, S.-H. Jung, M. Krings, C. Bolm, Angew. Chem. 2018, 130, 10883–10887; Angew. Chem. Int. Ed. 2018, 57, 10723–10727.

  • Altering Copper‐Catalyzed A3‐Couplings by Mechanochemistry: One‐Pot Synthesis of 1,4‐Diamino‐2‐butynes from Aldehydes, Amines, and Calcium Carbide
    M. Turberg, K. J. Ardila-Fierro, C. Bolm, J. G. Hernández, Angew. Chem. 2018, 130, 10878–10882; Angew. Chem. Int. Ed. 2018, 57, 10718–10722.

  • Synthesis of 3-Iodobenzofurans by Electrophilic Cyclization under Solventless Conditions in a Ball Mill
    A. C. Mantovani, J. G. Hernández, C. Bolm, Eur. J. Org. Chem. 2018, 2458–2461. Cover Feature: A. C. Mantovani, J. G. Hernández, C. Bolm, Eur. J. Org. Chem. 2018, 2296.

  • From Synthesis of Amino Acids and Peptides to Enzymatic Catalysis: A Bottom-Up Approach in Mechanochemistry
    C. Bolm, J. G. Hernández, ChemSusChem 2018, 11, 1410–1420.

  • Mechanochemical Cobalt‐Catalyzed C–H Bond Functionalizations by Ball Milling
    H. Cheng, J. G. Hernández, C. Bolm, Adv. Synth. Catal. 2018, 360, 1800–1804.

  • Mechanochemical dehydrocoupling of dimethylamine borane and hydrogenation reactions using Wilkinson's catalyst
    C. Schumacher, D. E. Crawford, B. Raguž, R. Glaum, S. L. James, C. Bolm, J. G. Hernández, Chem. Commun. 2018, 54, 8355–8358.

  • Papain-catalysed mechanochemical synthesis of oligopeptides by milling and twin-screw extrusion: application in the Juliá–Colonna enantioselective epoxidation
    K. J. Ardila-Fierro, D. E. Crawford, A. Körner, S. L. James, C. Bolm, J. G. Hernández, Green Chem. 2018, 20, 1262–1269.

  • Mechanochemical Oxidation and Cleavage of Lignin β-O-4 Model Compounds and Lignin
    S. Dabral, H. Wotruba, J. G. Hernández, C. Bolm, ACS Sustainable Chem. Eng. 2018, 6, 3242–3254.

  • Mechanochemical Activation of Iron Cyano Complexes: A Prebiotic Impact Scenario for the Synthesis of α-Amino Acid Derivatives
    C. Bolm, R. Mocci, C. Schumacher, M. Turberg, F. Puccetti, J. G. Hernández, Angew. Chem. 2018, 130, 2447–2450; Angew. Chem. Int. Ed. 2018, 57, 2423–2426. Selected as Very Important Paper. Highlighted in Chemistry World. Selected by Y. Uozumi and G. Hamasaka for Synfacts 2018, 14, 537.

  • Mechanochemical Rhodium(III)-Catalyzed C–H Bond Amidation of Arenes with Dioxazolones under Solventless Conditions in a Ball Mill
    G. N. Hermann, C. Bolm, ACS Catal. 2017, 7, 4592–4596.

  • Mechanoenzymatic peptide and amide bond formation
    J. G. Hernández, K. J. Ardila-Fierro, D. Crawford, S. L. James, C. Bolm, Green Chem. 2017, 19, 2620–2625.

  • Mechanochemical Indole Synthesis by Rhodium-Catalysed Oxidative Coupling of Acetanilides and Alkynes under Solventless Conditions in a Ball Mill
    G. N. Hermann, C. L. Jung, C. Bolm, Green Chem. 2017, 19, 2520–2523.

  • Mechanochemical Lignin-Mediated Strecker Reaction
    S. Dabral, M. Turberg, A. Wanninger, C. Bolm, J. G. Hernández, Molecules 2017, 22, 146.

  • Altering Product Selectivity by Mechanochemistry
    J. G. Hernández, C. Bolm, J. Org. Chem. 2017, 82, 4007–4019.

  • Mechanochemical Strecker Reaction: Access to α-Aminonitriles and Tetrahydroisoquinolines under Ball Milling Conditions
    J. G. Hernández, M. Turberg, I. Schiffers, C. Bolm, Chem. Eur. J. 2016, 22, 14513–14517.

  • Mechanochemical enzymatic kinetic resolution of secondary alcohols under ball-milling conditions
    J. G. Hernández, M. Frings, C. Bolm, ChemCatChem 2016, 8, 1769–1772.

  • Mechanochemical Iridium(III)-Catalyzed C-H Bond Amidations of Benzamides with Sulfonyl Azides under Solventless Conditions in Ball Mills
    G. N. Hermann, P. Becker, C. Bolm, Angew. Chem. 2016, 128, 3845–3848; Angew. Chem. Int. Ed. 2016, 55, 3781–3784. Selected as Very Important Paper.

  • [Cp*RhCl2]2: Mechanosynthesis and applications in C–H bond functionalisations under ball-milling conditions
    J. G. Hernández, C. Bolm, Chem. Commun. 2015, 51, 12582–12584.

  • Foreword
    C. Bolm in Ball Milling Towards Green Synthesis: Applications, Projects, Challenges, (Eds. A. Stolle, B. Ranu), The Royal Society of Chemistry 2015, pp vii - viii. DOI: 10.1039/9781782621980.

  • Mechanochemical Rhodium(III)-Catalyzed C–H Bond Functionali­zation of Acetanilides under Solventless Conditions in a Ball Mill
    G. N. Hermann, P. Becker, C. Bolm, Angew. Chem. 2015, 127, 7522–7525, Angew. Chem. Int. Ed. 2015, 54, 7414–7417.

  • Highlights from Faraday discussion 170: Challenges and opportunities of modern mechanochemistry, Montreal, Canada, 2014
    T. Friščić, S. L. James, E. V. Boldyreva, C. Bolm, W. Jones, J. Mack, J. W. Steed, K. S. Suslick, Chem. Commun. 2015, 51, 6248–6256.

  • Asymmetric Carbon Carbon Bond Formations under Solventless Conditions in Ball Mills
    M. Jörres, J. L. Aceña, V. A. Soloshonok, C. Bolm, ChemCatChem. 2015, 7, 1265–1269.

  • Mechanochemical degradation of lignin and wood by solvent-free grinding in a reactive medium
    T. Kleine, J. Buendia, C. Bolm, Green Chem. 2013, 15, 160–166.

  • Catalyzed organic reactions in ball mills
    A. Stolle, B. Ondruschka, A. Krebs, C. Bolm in Innovative Catalysis in Organic Synthesis - Oxidations, Hydrogenations, and C-X Bond Forming Reactions, (Ed. P. Andersson), Wiley-VCH, 2012, 327–349.

  • Organocatalytic Reactions: Effects of Ball Milling, Microwave and Ultrasound Irradiation
    A. Bruckmann, A. Krebs, C. Bolm, Green Chem. 2008, 10, 1131–1141.

  • Solvent-free asymmetric anhydride opening in a ball mill
    T. Rantanen, I. Schiffers, C. Bolm, Org. Process Res. Dev. 2007, 11, 592–597.

  • Solvent-Free Carbon-Carbon-Bond Formations in Ball Mills
    B. Rodríguez, T. Rantanen, A. Bruckmann, C. Bolm, Adv. Synth. Catal. 2007, 349, 2213–2233.

  • A Highly Efficient Asymmetric Organocatalytic Aldol Reaction in a Ball Mill
    B. Rodríguez, A. Bruckmann, C. Bolm, Chem. Eur. J. 2007, 13, 4710–4722.