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Literature DB >> 19170152

Oxindole synthesis by direct coupling of C(sp2)-H and C(sp3)-H centers.

Abstract

An sp(2)/sp(3) get-together: A novel and efficient method can be used to synthesize 3,3-disubstitued oxindoles by the direct intramolecular oxidative coupling of an aryl C(sp(2))-H and a C(sp(3))-H center (see scheme; DMF = N,N-dimethylformamide).

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Year: 2009 PMID： 19170152 DOI： 10.1002/anie.200805652

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

7 in total

1. Alpha-arylation of 3-aryloxindoles.

Authors: Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

2. Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.

Authors: Maxim Ratushnyy; Nikita Kvasovs; Sumon Sarkar; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2020-04-06 Impact factor: 15.336

3. Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp(2) C-H and sp(3) C-H bonds.

Authors: Nivesh Kumar; Santanu Ghosh; Subhajit Bhunia; Alakesh Bisai
Journal: Beilstein J Org Chem Date: 2016-06-08 Impact factor: 2.883

Oxindole synthesis by direct coupling of C(sp2)-H and C(sp3)-H centers.

1. Alpha-arylation of 3-aryloxindoles.

2. Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.

3. Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp(2) C-H and sp(3) C-H bonds.

4. A Cu-Catalysed Radical Cross-Dehydrogenative Coupling Approach to Acridanes and Related Heterocycles.

5. TBAI-Catalyzed Oxidative Coupling of Benzyl Ketones to Synthesize 2,3-Diaryl-1,4-Diketones in Water.

6. Oxindole synthesis via polar-radical crossover of ketene-derived amide enolates in a formal [3 + 2] cycloaddition.

7. Copper-catalyzed oxidative C(sp³)-H/C(sp²)-H cross-coupling en route to carbocyclic rings.