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Literature DB >> 19338010

Copper-catalyzed direct C arylation of heterocycles with aryl bromides: discovery of fluorescent core frameworks.

Dongbing Zhao¹, Wenhai Wang, Fei Yang, Jingbo Lan, Li Yang, Ge Gao, Jingsong You.

Abstract

A window of opportunity: A general copper-catalyzed C-H bond-activation path allows arylation of heterocycles with a wide range of aryl bromides (see scheme). The reaction shows excellent regioselectivity and exhibits good functional group tolerance. The 8-aryl xanthines exhibit fluorescence in a variety of solvents and show promise as reagents for biological imaging.

Entities: Chemical

Year: 2009 PMID： 19338010 DOI： 10.1002/anie.200900413

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

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Cited

8 in total

1. Catalyst- and solvent-free approach to 2-arylated quinolines via [5 + 1] annulation of 2-methylquinolines with diynones.

Authors: Hai-Yuan Zhao; Fu-Song Wu; Li Yang; Ying Liang; Xiao-Lin Cao; Heng-Shan Wang; Ying-Ming Pan
Journal: RSC Adv Date: 2018-01-25 Impact factor: 4.036

2. Purinyl N1-directed aromatic C-H oxidation in 6-arylpurines and 6-arylpurine nucleosides.

Authors: Raghu Ram Chamala; Damon Parrish; Padmanava Pradhan; Mahesh K Lakshman
Journal: J Org Chem Date: 2013-07-11 Impact factor: 4.354

3. Recent advances in direct C-H arylation: Methodology, selectivity and mechanism in oxazole series.

Authors: Cécile Verrier; Pierrik Lassalas; Laure Théveau; Guy Quéguiner; François Trécourt; Francis Marsais; Christophe Hoarau
Journal: Beilstein J Org Chem Date: 2011-11-29 Impact factor: 2.883

4. A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide.

Authors: Jevgenijs Tjutrins; Bruce A Arndtsen
Journal: Chem Sci Date: 2016-11-03 Impact factor: 9.825

5. Small organic molecules with tailored structures: initiators in the transition-metal-free C-H arylation of unactivated arenes.

Authors: Zhenghui Liu; Peng Wang; Yu Chen; Zhenzhong Yan; Suqing Chen; Wenjun Chen; Tiancheng Mu
Journal: RSC Adv Date: 2020-04-09 Impact factor: 4.036

Copper-catalyzed direct C arylation of heterocycles with aryl bromides: discovery of fluorescent core frameworks.

1. Catalyst- and solvent-free approach to 2-arylated quinolines via [5 + 1] annulation of 2-methylquinolines with diynones.

2. Purinyl N1-directed aromatic C-H oxidation in 6-arylpurines and 6-arylpurine nucleosides.

3. Recent advances in direct C-H arylation: Methodology, selectivity and mechanism in oxazole series.

4. A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide.

5. Small organic molecules with tailored structures: initiators in the transition-metal-free C-H arylation of unactivated arenes.

6. Copper-catalyzed CuAAC/intramolecular C-H arylation sequence: Synthesis of annulated 1,2,3-triazoles.

7. C-H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C-H activation.

8. Copper-catalyzed remote C-H arylation of polycyclic aromatic hydrocarbons (PAHs).