Enantiospecific synthesis of [2.2]paracyclophane-4-thiol and derivatives

Scholarly Works

• Patel, S.; Dais, T. N.; Plieger, P. G.; Rowlands, G. J. Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes. Beilstein journal of organic chemistry 2021, 17, 1518–1526. doi:10.3762/bjoc.17.109
• Mungalpara, M. N.; Plieger, P. G.; Rowlands, G. J. The Synthesis of Pyridyl[2.2]paracyclophanes by Palladium‐Catalyzed Cross‐Coupling of Pyridine Sulfinates. Advanced Synthesis & Catalysis 2020, 363, 1069–1080. doi:10.1002/adsc.202001429
• Hassan, Z.; Spuling, E.; Knoll, D. M.; Bräse, S. Regioselective Functionalization of [2.2]Paracyclophanes: Recent Synthetic Progress and Perspectives. Angewandte Chemie (International ed. in English) 2019, 59, 2156–2170. doi:10.1002/anie.201904863
• Hassan, Z.; Spuling, E.; Knoll, D. M.; Bräse, S. Regioselektive Funktionalisierung von [2.2]Paracyclophanen: aktuelle Synthesefortschritte und Perspektiven. Angewandte Chemie 2019, 132, 2176–2190. doi:10.1002/ange.201904863
• Knoll, D. M.; Wiesner, T.; Marschner, S. M.; Hassan, Z.; Weis, P.; Kappes, M. M.; Nieger, M.; Bräse, S. Synthesis and characterization of rigid [2.2]paracyclophane–porphyrin conjugates as scaffolds for fixed-distance bimetallic complexes. RSC advances 2019, 9, 30541–30544. doi:10.1039/c9ra07055a
• Mungalpara, M. N.; Wang, J.; Coles, M. P.; Plieger, P. G.; Rowlands, G. J. The synthesis of a [2.2]paracyclophane-derived secondary phosphine oxide and a study of its reactivity. Tetrahedron 2018, 74, 5519–5527. doi:10.1016/j.tet.2018.05.013
• Shii, T.; Hatori, M.; Yokota, K.; Hattori, Y.; Kimura, M. Selective Blocking Property of Microporous Polymer Membranes Fabricated by Chemical Vapor Deposition. Scientific reports 2017, 7, 15596. doi:10.1038/s41598-017-15470-x
• Jayasundera, K. P.; Engels, T. G. W.; Lun, D. J.; Mungalpara, M. N.; Plieger, P. G.; Rowlands, G. J. The synthesis of planar chiral pseudo-gem aminophosphine pre-ligands based on [2.2]paracyclophane. Organic & biomolecular chemistry 2017, 15, 8975–8984. doi:10.1039/c7ob02393f
• Braun, C.; Nieger, M.; Thiel, W. R.; Bräse, S. [2.2]Paracyclophanes with N‐Heterocycles as Ligands for Mono‐ and Dinuclear Ruthenium(II) Complexes. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 15474–15483. doi:10.1002/chem.201703291
• Jayasundera, K. P.; Kusmus, D. N. M.; Deuilhé, L.; Etheridge, L.; Farrow, Z.; Lun, D. J.; Kaur, G.; Rowlands, G. J. The synthesis of substituted amino[2.2]paracyclophanes. Organic & biomolecular chemistry 2016, 14, 10848–10860. doi:10.1039/c6ob02150f
• Schlindwein, S. H.; Bader, K.; Sibold, C.; Frey, W.; Neugebauer, P.; Orlita, M.; van Slageren, J.; Gudat, D. New Selective Synthesis of Dithiaboroles as a Viable Pathway to Functionalized Benzenedithiolenes and Their Complexes. Inorganic chemistry 2016, 55, 6186–6194. doi:10.1021/acs.inorgchem.6b00821
• Vincent, A.; Deschamps, D.; Martzel, T.; Lohier, J. F.; Richards, C. J.; Gaumont, A.-C.; Perrio, S. Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary. The Journal of organic chemistry 2016, 81, 3961–3966. doi:10.1021/acs.joc.6b00560
• Braun, C.; Spuling, E.; Heine, N. B.; Cakici, M.; Nieger, M.; Bräse, S. Efficient Modular Synthesis of Isomeric Mono- and Bispyridyl[2.2]paracyclophanes by Palladium-Catalyzed Cross- Coupling Reactions. Advanced Synthesis & Catalysis 2016, 358, 1664–1670. doi:10.1002/adsc.201600066
• Gelat, F.; Lohier, J.-F.; Gaumont, A.-C.; Perrio, S. tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts. Advanced Synthesis & Catalysis 2015, 357, 2011–2016. doi:10.1002/adsc.201500368
• Thennakoon, N.; Kaur, G.; Wang, J.; Plieger, P. G.; Rowlands, G. J. An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis. Australian Journal of Chemistry 2015, 68, 566–575. doi:10.1071/ch14548
• Atman, N. V.; Zhuravsky, R. P.; Antonov, D. Y.; Sergeeva, E. V.; Godovikov, I. A.; Starikova, Z. A.; Vologzhanina, A. V. Synthesis of Bromo-Substituted 4-Hydroxy[2.2]paracyclophanes and [2.2]Paracyclophane-4,7-quinones as Versatile Chiral Building Blocks. European Journal of Organic Chemistry 2014, 2015, 325–330. doi:10.1002/ejoc.201403316
• Beqa, L.; Deschamps, D.; Perrio, S.; Gaumont, A.-C.; Knoppe, S.; Buergi, T. Ligand Exchange Reaction on Au38(SR)24, Separation of Au38(SR)23(SR′)1 Regioisomers, and Migration of Thiolates. The Journal of Physical Chemistry C 2013, 117, 21619–21625. doi:10.1021/jp408455x
• Glover, J. E.; Martin, D. J.; Plieger, P. G.; Rowlands, G. J. Planar Chiral Triazole‐Based Phosphanes Derived from [2.2]Paracyclophane and Their Activity in Suzuki Coupling Reactions. European Journal of Organic Chemistry 2013, 2013, 1671–1675. doi:10.1002/ejoc.201201601
• Lennartz, P.; Raabe, G.; Bolm, C. Palladium‐Catalyzed CH Bond Acetoxylation: An Approach to ortho‐Substituted Hydroxy[2.2]paracyclophane Derivatives. Advanced Synthesis & Catalysis 2012, 354, 3237–3249. doi:10.1002/adsc.201200625
• Enders, D.; Ludwig, M.; Raabe, G. Synthesis and application of the first planar chiral strong Brønsted acid organocatalysts. Chirality 2012, 24, 215–222. doi:10.1002/chir.21985

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