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Literature DB >> 14518978

Cyclohexane and benzene amination by catalytic nitrene insertion into C-H bonds with the copper-homoscorpionate catalyst TpBr3CuNCMe.

M Mar Díaz-Requejo¹, Tomás R Belderraín, M Carmen Nicasio, Swiatoslaw Trofimenko, Pedro J Pérez.

Abstract

The complex TpBr3Cu(NCMe) catalyzes, at room temperature, the insertion of a nitrene group from PhINTs into the carbon-hydrogen bond of cyclohexane and benzene, as well as into the primary C-H bonds of the methyl groups of toluene and mesitylene, in moderate to high yield.

Entities: Chemical

Year: 2003 PMID： 14518978 DOI： 10.1021/ja037072l

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

10 in total

1. Pd-catalyzed aryl C-H imidation with arene as the limiting reagent.

Authors: Gregory B Boursalian; Ming-Yu Ngai; Katarzyna N Hojczyk; Tobias Ritter
Journal: J Am Chem Soc Date: 2013-09-03 Impact factor: 15.419

2. Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.

Authors: Jun Pan; Mingjuan Su; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2011-08-02 Impact factor: 15.336

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Authors: Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal: Chem Rev Date: 2019-01-30 Impact factor: 60.622

Cyclohexane and benzene amination by catalytic nitrene insertion into C-H bonds with the copper-homoscorpionate catalyst TpBr3CuNCMe.

1. Pd-catalyzed aryl C-H imidation with arene as the limiting reagent.

2. Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

4. Examination of the mechanism of Rh(2)(II)-catalyzed carbazole formation using intramolecular competition experiments.

5. Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination.

6. Rhodium(ii)-catalyzed C-H aminations using N-mesyloxycarbamates: reaction pathway and by-product formation.

7. Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

8. Cu(I)-catalyzed C-H alpha-amination of aryl ketones: direct synthesis of imidazolinones.

9. Lewis acid trapping of an elusive copper-tosylnitrene intermediate using scandium triflate.

Review 10. Challenges and opportunities for alkane functionalisation using molecular catalysts.

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Review 10. Challenges and opportunities for alkane functionalisation using molecular catalysts.

Review 3. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.