Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp² C–H bond activation in ball mills

Scholarly Works

• Adak, L.; Roy, K.; Saha, A.; Sahoo, S.; Banerjee, S.; Mukhopadhyay, C. D.; Banerjee, S. Reaction under Ball-Milling: Solvent- and Metal-Free One-Pot Diastereoselective Synthesis of Tetrahydroquinoline Derivatives as Potential Antibacterial and Anticancer Agents. Synlett 2024. doi:10.1055/a-2378-1847
• Borodkin, G. I. Mechanochemical synthesis of organohalogen compounds: a synthetic chemist's view. Russian Chemical Reviews 2023, 92, RCR5091. doi:10.59761/rcr5091
• Akhlaghi, Z.; Naimi-Jamal, M. R.; Panahi, L.; Dekamin, M. G.; Farasati Far, B. Solvent-free mechanochemical multicomponent preparation of 4H-pyrans catalyzed by Cu2(NH2-BDC)2(DABCO) metal-organic framework. Heliyon 2023, 9, e13522. doi:10.1016/j.heliyon.2023.e13522
• Roy, K.; Sahoo, S.; Saha, A.; Adak, L. Ball Milling in Organic Transformations. Current Organic Chemistry 2023, 27, 153–165. doi:10.2174/1385272827666221223143844
• Das, D.; Bhosle, A. A.; Chatterjee, A.; Banerjee, M. Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides. Beilstein journal of organic chemistry 2022, 18, 999–1008. doi:10.3762/bjoc.18.100
• Ardila‐Fierro, K. J.; Vugrin, L.; Halasz, I.; Palčić, A.; Hernández, J. G. Mechanochemical Bromination of Naphthalene Catalyzed by Zeolites: From Small Scale to Continuous Synthesis. Chemistry–Methods 2022, 2. doi:10.1002/cmtd.202200035
• Barišić, D.; Pajić, M.; Halasz, I.; Babić, D.; Ćurić, M. Mechanochemical halogenation of unsymmetrically substituted azobenzenes. Beilstein journal of organic chemistry 2022, 18, 680–687. doi:10.3762/bjoc.18.69
• Barišić, D.; Halasz, I.; Bjelopetrović, A.; Babić, D.; Ćurić, M. Mechanistic Study of the Mechanochemical PdII-Catalyzed Bromination of Aromatic C–H Bonds by Experimental and Computational Methods. Organometallics 2022, 41, 1284–1294. doi:10.1021/acs.organomet.1c00698
• Bhawani; Shinde, V. N.; Sonam; Rangan, K.; Kumar, A. Mechanochemical Ruthenium-Catalyzed Ortho-Alkenylation of N-Heteroaryl Arenes with Alkynes under Ball-Milling Conditions. The Journal of organic chemistry 2022, 87, 5994–6005. doi:10.1021/acs.joc.2c00257
• Ardila-Fierro, K. J.; Rubčić, M.; Hernández, J. G. Cocrystal Formation Precedes the Mechanochemically Acetate-Assisted C-H Activation with [Cp*RhCl2 ]2. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202200737. doi:10.1002/chem.202200737
• Laskar, R.; Pal, T.; Bhattacharya, T.; Maiti, S.; Akita, M.; Maiti, D. Sustainable C–H functionalization under ball-milling, microwave-irradiation and aqueous media. Green Chemistry 2022, 24, 2296–2320. doi:10.1039/d1gc04530j
• Farshadfar, K.; Tizhoush, S. K.; Ariafard, A. Role of Brønsted Acids in Promoting Pd(OAc)2-Catalyzed Chlorination of Phenol Carbamates Using N-Chlorosuccinimide. ACS Catalysis 2022, 12, 2681–2693. doi:10.1021/acscatal.1c05512
• Williams, M.; Morrill, L. C.; Browne, D. L. Mechanochemical Organocatalysis: Do High Enantioselectivites Contradict what we Might Expect?. ChemSusChem 2021, 15, e202102157. doi:10.1002/cssc.202102157
• Zhou, K.; Mao, Y.; Wu, F.; Lou, S.; Xu, D. Recent Advances in C—H Bond Functionalization under Mechanochemical Conditions. Chinese Journal of Organic Chemistry 2021, 41, 4623. doi:10.6023/cjoc202106046
• Huang, Y.-H.; Wang, S.-R.; Wu, D.-P.; Huang, P.-Q. Intermolecular Dehydrative [4 + 2] Aza-Annulation of N-Arylamides with Alkenes: A Direct and Divergent Entrance to Aza-Heterocycles. Organic letters 2019, 21, 1681–1685. doi:10.1021/acs.orglett.9b00233
• Xu, H.; Fan, G.-P.; Liu, Z.; Wang, G.-W. Catalyst- and solvent-free mechanochemical synthesis of isoxazoles from N-hydroxybenzimidoyl chlorides and enamino carbonyl compounds. Tetrahedron 2018, 74, 6607–6611. doi:10.1016/j.tet.2018.09.044
• Li, L.; Wang, G.-W. Solvent-free rhodium(III)-catalyzed synthesis of 2-aminoanilides via C−H amidation of N-nitrosoanilines under ball-milling conditions. Tetrahedron 2018, 74, 4188–4196. doi:10.1016/j.tet.2018.06.003
• Xu, H.; Liu, H.-W.; Chen, K.; Wang, G.-W. One-Pot Multicomponent Mechanosynthesis of Polysubstituted trans-2,3-Dihydropyrroles and Pyrroles from Amines, Alkyne Esters, and Chalcones. The Journal of organic chemistry 2018, 83, 6035–6049. doi:10.1021/acs.joc.8b00665
• Xu, H.; Chen, K.; Liu, H.-W.; Wang, G.-W. Solvent-free N-iodosuccinimide-promoted synthesis of spiroimidazolines from alkenes and amidines under ball-milling conditions. Organic Chemistry Frontiers 2018, 5, 2864–2869. doi:10.1039/c8qo00723c

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