Supporting Information
Full experimental details and analytical data (1H NMR, 13C NMR, X-ray analysis) are provided in the following files.
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| Supporting Information File 2: Spectra. | ||
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| Supporting Information File 3: RInChIs. | ||
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| Supporting Information File 4: DOIs data repository. | ||
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| Supporting Information File 5: Reference samples molecule archive. | ||
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Cite the Following Article
Insertion of [1.1.1]propellane into aromatic disulfides
Robin M. Bär, Gregor Heinrich, Martin Nieger, Olaf Fuhr and Stefan Bräse
Beilstein J. Org. Chem. 2019, 15, 1172–1180.
https://doi.org/10.3762/bjoc.15.114
How to Cite
Bär, R. M.; Heinrich, G.; Nieger, M.; Fuhr, O.; Bräse, S. Beilstein J. Org. Chem. 2019, 15, 1172–1180. doi:10.3762/bjoc.15.114
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- Hu, Q.-Q.; Chen, J.; Yang, Y.; Yang, H.; Zhou, L. Strain-release transformations of bicyclo[1.1.0]butanes and [1.1.1]propellanes. Tetrahedron Chem 2024, 9, 100070. doi:10.1016/j.tchem.2024.100070
- Das, K.; Pedada, A.; Singha, T.; Hari, D. P. Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and - lactams. Chemical science 2024, 15, 3182–3191. doi:10.1039/d3sc05700c
- Gupta, S.; Srinivasu, V.; Sureshkumar, D. Metal and catalyst-free strategy to access 1,3-thio-heteroaryl BCP derivatives. Organic & biomolecular chemistry 2023, 21, 8136–8140. doi:10.1039/d3ob01377d
- Wang, C.-S.; Xu, Y.; Zhou, Y.-L.; Zheng, C.-L.; Wang, G.; Sun, Q. Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization. Organic Chemistry Frontiers 2023, 10, 4972–5027. doi:10.1039/d3qo00933e
- Zhao, X.; Shou, J.-Y.; Qing, F.-L. Iodopentafluorosulfanylation of [1.1.1]propellane and further functionalizations. Science China Chemistry 2023, 66, 2871–2877. doi:10.1007/s11426-023-1715-2
- Iida, T.; Kanazawa, J.; Matsunaga, T.; Miyamoto, K.; Hirano, K.; Uchiyama, M. Practical and Facile Access to Bicyclo[3.1.1]heptanes: Potent Bioisosteres of meta-Substituted Benzenes. Journal of the American Chemical Society 2022, 144, 21848–21852. doi:10.1021/jacs.2c09733
- Kraemer, Y.; Ghiazza, C.; Ragan, A. N.; Ni, S.; Lutz, S.; Neumann, E. K.; Fettinger, J. C.; Nöthling, N.; Goddard, R.; Cornella, J.; Pitts, C. R. Strain‐Release Pentafluorosulfanylation and Tetrafluoro(aryl)sulfanylation of [1.1.1]Propellane: Reactivity and Structural Insight**. Angewandte Chemie 2022, 134. doi:10.1002/ange.202211892
- Kraemer, Y.; Ghiazza, C.; Ragan, A. N.; Ni, S.; Lutz, S.; Neumann, E. K.; Fettinger, J. C.; Nöthling, N.; Goddard, R.; Cornella, J.; Pitts, C. R. Strain-Release Pentafluorosulfanylation and Tetrafluoro(aryl)sulfanylation of [1.1.1]Propellane: Reactivity and Structural Insight. Angewandte Chemie (International ed. in English) 2022, 61, e202211892. doi:10.1002/anie.202211892
- Livesley, S.; Trueman, B.; Robertson, C. M.; Goundry, W. R. F.; Morris, J. A.; Aïssa, C. Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane. Organic letters 2022, 24, 7015–7020. doi:10.1021/acs.orglett.2c02875
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- He, F.-S.; Xie, S.; Yao, Y.; Wu, J. Recent advances in the applications of [1.1.1]propellane in organic synthesis. Chinese Chemical Letters 2020, 31, 3065–3072. doi:10.1016/j.cclet.2020.04.023
- Wu, Z.; Xu, Y.; Wu, X.; Zhu, C. Synthesis of selenoether and thioether functionalized bicyclo[1.1.1]pentanes. Tetrahedron 2020, 76, 131692. doi:10.1016/j.tet.2020.131692
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- Andersen, C.; Ferey, V.; Daumas, M.; Bernardelli, P.; Guérinot, A.; Cossy, J. Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents. Organic letters 2020, 22, 6021–6025. doi:10.1021/acs.orglett.0c02115
- Steinbeck, C.; Koepler, O.; Bach, F.; Herres-Pawlis, S.; Jung, N.; Liermann, J. C.; Neumann, S.; Razum, M.; Baldauf, C.; Biedermann, F.; Bocklitz, T.; Boehm, F.; Broda, F.; Czodrowski, P.; Engel, T.; Hicks, M. G.; Kast, S.; Kettner, C.; Koch, W.; Lanza, G.; Link, A.; Mata, R.; Nagel, W. E.; Porzel, A.; Schlörer, N.; Schulze, T.; Weinig, H.-G.; Wenzel, W.; Wessjohann, L. A.; Wulle, S. NFDI4Chem - Towards a National Research Data Infrastructure for Chemistry in Germany. Research Ideas and Outcomes 2020, 6. doi:10.3897/rio.6.e55852
- Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Visible Light-Driven Radical-Mediated C-C Bond Cleavage/Functionalization in Organic Synthesis. Chemical reviews 2020, 121, 506–561. doi:10.1021/acs.chemrev.0c00030