Late-stage functionalization

Late-stage functionalization (LSF) is a desired, chemical or biochemical, chemoselective transformation on a complex molecule to provide at least one analog in sufficient quantity and purity for a given purpose without needing the addition of a functional group that exclusively serves to enable said transformation.[1]

Molecular complexity is an intrinsic property of each molecule and frequently determines the synthetic effort to make it.[2][3] LSF can significantly diminish this synthetic effort, and thus enables access to molecules, which would otherwise not be available or too difficult to access. The requirements for LSF can be met by both C–H functionalization reactions and functional group manipulations.[1] LSF reactions are particularly relevant and often used in the fields of drug discovery and materials chemistry,[4][5][6] although no LSF has been implemented in a commercial process.

  1. ^ a b Börgel, Jonas; Ritter, Tobias (2020-08-06). "Late-Stage Functionalization". Chem. 6 (8): 1877–1887. Bibcode:2020Chem....6.1877B. doi:10.1016/j.chempr.2020.07.007. ISSN 2451-9294.
  2. ^ von Korff, Modest; Sander, Thomas (2019-01-30). "Molecular Complexity Calculated by Fractal Dimension". Scientific Reports. 9 (1): 967. Bibcode:2019NatSR...9..967V. doi:10.1038/s41598-018-37253-8. ISSN 2045-2322. PMC 6353876. PMID 30700728.
  3. ^ Corey, E. J.; Wipke, W. Todd (1969-10-10). "Computer-Assisted Design of Complex Organic Syntheses". Science. 166 (3902): 178–192. Bibcode:1969Sci...166..178C. doi:10.1126/science.166.3902.178. ISSN 0036-8075. PMID 17731475.
  4. ^ Cernak, Tim; Dykstra, Kevin D.; Tyagarajan, Sriram; Vachal, Petr; Krska, Shane W. (2016-02-01). "The medicinal chemist's toolbox for late stage functionalization of drug-like molecules". Chemical Society Reviews. 45 (3): 546–576. doi:10.1039/C5CS00628G. ISSN 1460-4744. PMID 26507237.
  5. ^ Moir, Michael; Danon, Jonathan J.; Reekie, Tristan A.; Kassiou, Michael (2019-11-02). "An overview of late-stage functionalization in today's drug discovery". Expert Opinion on Drug Discovery. 14 (11): 1137–1149. doi:10.1080/17460441.2019.1653850. hdl:1885/213256. ISSN 1746-0441. PMID 31411499. S2CID 199572352.
  6. ^ Wencel-Delord, Joanna; Glorius, Frank (2013-04-23). "C–H bond activation enables the rapid construction and late-stage diversification of functional molecules". Nature Chemistry. 5 (5): 369–375. Bibcode:2013NatCh...5..369W. doi:10.1038/nchem.1607. ISSN 1755-4349. PMID 23609086.
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