Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds

  title={Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds},
  author={Nivesh Kumar and Santanu Ghosh and Subhajit Bhunia and A. Bisai},
  journal={Beilstein Journal of Organic Chemistry},
  pages={1153 - 1169}
The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a ‘transition-metal-free’ intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon–carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path… Expand
Low-Temperature, Transition-Metal-Free Cross-Dehydrogenative Coupling Protocol for the Synthesis of 3,3-Disubstituted Oxindoles.
A new low-temperature procedure for the synthesis of 3,3-disubstituted 2-oxindoles via cross-dehydrogenative coupling (CDC) is reported, and new evidence suggests that this transformation may occur via a transiently stable iodinated intermediate rather than by direct single-electron oxidation. Expand
Heterocycles via Cross Dehydrogenative Coupling: Synthesis and Functionalization
Nitrogen-containing heterocycles are a ubiquitous nature and synthetic compounds having wide spectrum of activities, which has found applications in various industrial fields. Among a variety ofExpand
Synthesis and Functionalization of N-Heterocycles Using Transition Metal-Free Cross-Dehydrogenative Coupling (CDC) Approaches
The creation of carbon–carbon bonds for the construction or the post-functionalization of various N-heterocycles is one of the most active research areas in organic chemistry. Among those approaches,Expand
C–H Functionalization/activation in organic synthesis
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  • Beilstein journal of organic chemistry
  • 2016
The last decade has seen an explosion in research reports in the area of C–H functionalization/activation in organic synthesis, but it took many in the synthetic organic community this long to fully embrace this exciting and enabling technology. Expand
Deacylative Alkylation vs. Photoredox Catalysis in the Synthesis of 3,3'-Bioxindoles
We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovacion y Universidades (projects CTQ2016-81893REDT, and RED2018-102387-T) the Spanish Ministerio de Economia,Expand
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Intramolecular Dehydrogenative Coupling Approach to 2‐Oxindoles Using Fe(OAc) 2 /NaI/Na 2 S 2 O 8
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  • 2020


Intramolecular dehydrogenative coupling of sp2 C-H and sp3 C-H bonds: an expeditious route to 2-oxindoles.
An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternaryExpand
Oxidative dimerization of 2-oxindoles promoted by KO(t)Bu-I₂: total synthesis of (±)-folicanthine.
A 'transition-metal-free' oxidative coupling of 2-oxindoles has been demonstrated in the presence of 1.2 equiv each of potassium tert-butoxide and iodine. The method yields a diverse range ofExpand
First C-H activation route to oxindoles using copper catalysis.
The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described and a key intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described. Expand
Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation.
This critical review covers the recent progresses on the regioselective dehydrogenative direct coupling reaction of heteroarenes, including arylation, olefination, alkynylation, and amination/amidation mainly utilizing transition metal catalysts. Expand
Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.
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  • Medicine, Chemistry
  • Proceedings of the National Academy of Sciences of the United States of America
  • 2006
Various sp, sp(2), and sp(3) C-H bonds of pronucleophiles were used in the Cu-catalyzed CDC reactions and the mechanisms of the CDC reactions are discussed. Expand
Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization.
Mechanistic investigations indicate that the reaction proceeds via nucleophilic attack of the phthalimide on an aromatic radical cation, as opposed to the electrophilic aromatic amination that has been reported for other I(III) amination reactions. Expand
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A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope andExpand
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Total synthesis of (+)-lyconadin A and related compounds via oxidative C-N bond formation.
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A two-fold Pd-catalyzed decarboxylative allylic alkylation is used to construct two vicinal all carbon quaternary stereocenters in a diastereo- and enantioselective fashion to complete the formal syntheses of the cyclotryptamine alkaloids. Expand