- Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols
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A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50–92 % yield, 79 % average yield).
- Dambatta, Mubarak B.,Polidano, Kurt,Northey, Alexander D.,Williams, Jonathan M. J.,Morrill, Louis C.
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p. 2345 - 2349
(2019/05/16)
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- Transition-metal-free Chemoselective Oxidative C?C Coupling of the sp3 C?H Bond of Oxindoles with Arenes and Addition to Alkene: Synthesis of 3-Aryl Oxindoles, and Benzofuro- and Indoloindoles
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A transition-metal (TM)-free and halogen-free NaOtBu-mediated oxidative cross-coupling between the sp3 C?H bond of oxindoles and sp2 C?H bond of nitroarenes has been developed to access 3-aryl substituted and 3,3-aryldisubstituted oxindoles in DMSO at room temperature in a short time. Interestingly, the sp3 C?H bond of oxindoles could also react with styrene under TM-free conditions for the practical synthesis of quaternary 3,3-disubstituted oxindoles. The synthesized 3-oxindoles have also been further transformed into advanced heterocycles, that is, benzofuroindoles, indoloindoles, and substituted indoles. Mechanistic experiments of the reaction suggests the formation of an anion intermediate from the sp3 C?H bond of oxindole by tert-butoxide base in DMSO. The addition of nitrobenzene to the in-situ generated carbanion leads to the 3-(nitrophenyl)oxindolyl carbanion in DMSO which is subsequently oxidized to 3-(nitro-aryl) oxindole by DMSO.
- Sattar, Moh.,Rathore, Vandana,Prasad, Ch. Durga,Kumar, Sangit
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supporting information
p. 734 - 743
(2017/04/13)
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- Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols
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A palladium complex sequentially promoted two mechanistically distinct reactions, the first, cyclization of 2-(alkynyl)aryl isocyanates with benzylic alcohols, and the second, [1,3] rearrangement of a benzyl group from oxygen to carbon, furnishing 3,3-dis
- Toyoshima, Takeharu,Mikano, Yusuke,Miura, Tomoya,Murakami, Masahiro
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supporting information; experimental part
p. 4584 - 4587
(2010/12/25)
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- Iridium catalysed C-3 alkylation of oxindole with alcohols under solvent free thermal or microwave conditions
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Ir-catalysed alkylation of oxindole and N-methyl oxindole with a range of substituted benzyl and heteroaryl alcohols under solvent free thermal or microwave conditions afforded the corresponding C-3-monoalkylated products in high to excellent yield.
- Grigg, Ronald,Whitney, Simon,Sridharan, Visuvanathar,Keep, Ann,Derrick, Andrew
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experimental part
p. 4375 - 4383
(2009/10/17)
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