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Literature DB >> 26016723

Iodine-catalyzed sp³ C-H bond activation by selenium dioxide: synthesis of diindolylmethanes and di(3-indolyl)selanides.

P Seetham Naidu¹, Swarup Majumder¹, Pulak J Bhuyan².

Abstract

An efficient reaction protocol was developed for the synthesis of several diindolylmethane derivatives via the [Formula: see text] C-H bond activation of aryl methyl ketones by [Formula: see text] and indoles in the presence of catalytic amounts of [Formula: see text] at 80 [Formula: see text] using dioxane as solvent. Unexpectedly, an interesting class of di(3-indolyl)selenide compounds was isolated when the reaction was carried out at room temperature.

Entities: Chemical

Keywords: C–H activation; Diindolylmethanes; Indole; Indolylselanides; Iodine; Selanides

Mesh：

Substances：

Year: 2015 PMID： 26016723 DOI： 10.1007/s11030-015-9605-3

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

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1. Iodine-mediated sp³ C-H functionalization of methyl ketones: a one-pot synthesis of functionalized indolizines via the 1,3-dipolar cycloaddition reaction between pyridinium ylides and ynones.

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1 in total

Iodine-catalyzed sp³ C-H bond activation by selenium dioxide: synthesis of diindolylmethanes and di(3-indolyl)selanides.

1. Activation of Cminus signH Bonds by Metal Complexes.

2. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

3. Dynamic pharmacophore model optimization: identification of novel HIV-1 integrase inhibitors.

4. Intramolecular 1,3-dipolar cycloaddition reactions in the synthesis of complex annelated quinolines, α-carbolines and coumarins.

5. Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus.

6. Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells.

7. Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

8. Bcl-2 family-mediated apoptotic effects of 3,3'-diindolylmethane (DIM) in human breast cancer cells.

9. 3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells.

10. sp3 C-H bond arylation directed by amidine protecting group: alpha-arylation of pyrrolidines and piperidines.

1. Iodine-mediated sp³ C-H functionalization of methyl ketones: a one-pot synthesis of functionalized indolizines via the 1,3-dipolar cycloaddition reaction between pyridinium ylides and ynones.