Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 9, Pages 6172-6180Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00370
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Funding
- Synthesis and Solid State Pharmaceutical Centre (SSPC) - Science Foundation Ireland (SFI) [12/RC/2275]
- BEACON postdoctoral fellowship [16/RC/23889]
- Irish Research Council (IRC) [GOIPD/2015/453]
- Higher Education Authority's PRTLI
- SSPC [GOIPD/2015/453]
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alpha-Aryl oxindoles are accessed from isatin via a two-step procedure involving a phospha-Brook rearrangement and a Friedel-Crafts alkylation in a one-pot procedure. The use of 1,1,1,3,3,3-hexafluoro-2-propanol as solvent significantly extended the reaction substrate scope to include relatively less electron-rich arenes including benzene. This new alkylation method is fast and straightforward and allows for the direct introduction of the oxindole moiety onto a range of aromatic compounds including phenols. Additionally, the application of arylated products was shown in decarboxylative asymmetric allylation and protonation.
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