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Literature DB >> 17616203

C-C bond formation via double C-H functionalization: aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls.

Timothy A Dwight¹, Nicholas R Rue, Dagmara Charyk, Ryan Josselyn, Brenton DeBoef.

Abstract

The aerobic oxidative coupling of arenes such as benzofuran and N-substituted indoles with benzene and derivatives thereof is described. The reaction is shown to take place in both inter- and intramolecular scenarios.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17616203 PMCID： PMC2566853 DOI： 10.1021/ol071308z

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

13 in total

1. Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization.

Authors: Neil P Grimster; Carolyn Gauntlett; Christopher R A Godfrey; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2005-05-13 Impact factor: 15.336

2. Room temperature palladium-catalyzed 2-arylation of indoles.

Authors: Nicholas R Deprez; Dipannita Kalyani; Andrew Krause; Melanie S Sanford
Journal: J Am Chem Soc Date: 2006-04-19 Impact factor: 15.419

3. Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design.

Authors: Marc Lafrance; Keith Fagnou
Journal: J Am Chem Soc Date: 2006-12-27 Impact factor: 15.419

4. Palladium-catalyzed C-H homocoupling of bromothiophene derivatives and synthetic application to well-defined oligothiophenes.

Authors: Masabumi Takahashi; Kentaro Masui; Hiroki Sekiguchi; Nobuhiko Kobayashi; Atsunori Mori; Masahiro Funahashi; Nobuyuki Tamaoki
Journal: J Am Chem Soc Date: 2006-08-23 Impact factor: 15.419

5. Mild and general conditions for the cross-coupling of aryl halides with pentafluorobenzene and other perfluoroaromatics.

Authors: Marc Lafrance; Daniel Shore; Keith Fagnou
Journal: Org Lett Date: 2006-10-26 Impact factor: 6.005

6. Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations.

Authors: Kami L Hull; Erica L Lanni; Melanie S Sanford
Journal: J Am Chem Soc Date: 2006-11-01 Impact factor: 15.419

7. Direct palladium-catalyzed C-2 and C-3 arylation of indoles: a mechanistic rationale for regioselectivity.

Authors: Benjamin S Lane; Meghann A Brown; Dalibor Sames
Journal: J Am Chem Soc Date: 2005-06-08 Impact factor: 15.419

8. Oxidative coupling of benzenes with alpha,beta-unsaturated aldehydes by the Pd(OAc)2/molybdovanadophosphoric acid/O2 system.

Authors: Tomoyuki Yamada; Satoshi Sakaguchi; Yasutaka Ishii
Journal: J Org Chem Date: 2005-07-08 Impact factor: 4.354

C-C bond formation via double C-H functionalization: aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls.

1. Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization.

2. Room temperature palladium-catalyzed 2-arylation of indoles.

3. Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design.

4. Palladium-catalyzed C-H homocoupling of bromothiophene derivatives and synthetic application to well-defined oligothiophenes.

5. Mild and general conditions for the cross-coupling of aryl halides with pentafluorobenzene and other perfluoroaromatics.

6. Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations.

7. Direct palladium-catalyzed C-2 and C-3 arylation of indoles: a mechanistic rationale for regioselectivity.

8. Oxidative coupling of benzenes with alpha,beta-unsaturated aldehydes by the Pd(OAc)2/molybdovanadophosphoric acid/O2 system.

9. The catalytic cross-coupling of unactivated arenes.

10. Palladium-catalyzed arylation and heteroarylation of indolizines.

1. Direct arylation of 6-phenylpurine and 6-arylpurine nucleosides by ruthenium-catalyzed C-H bond activation.

2. Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.

3. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

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

5. Copper-catalyzed arylation of heterocycle C-H bonds.

6. Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization.

7. Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

8. A general method for copper-catalyzed arene cross-dimerization.

9. Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

10. A general method for copper-catalyzed arylation of arene C-H bonds.