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Literature DB >> 21699210

Direct arylation of polycyclic aromatic hydrocarbons through palladium catalysis.

Kenji Mochida¹, Katsuaki Kawasumi, Yasutomo Segawa, Kenichiro Itami.

Abstract

We have discovered that the combination of Pd(OAc)(2)/o-chloranil can catalyze the direct C-H bond arylation of polycyclic aromatic hydrocarbons (PAHs) with arylboroxins that occurs selectively at the K-region. The sequential integration of Pd-catalyzed direct arylation of PAHs and FeCl(3)-mediated cyclodehydrogenation is effective in rapidly extending a parent PAH π-system with high directionality.

Entities: Chemical

Year: 2011 PMID： 21699210 DOI： 10.1021/ja202975w

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

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Cited

13 in total

1. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules.

Authors: Joanna Wencel-Delord; Frank Glorius
Journal: Nat Chem Date: 2013-05 Impact factor: 24.427

2. Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

Authors: Keary M Engle; Peter S Thuy-Boun; Michael Dang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2011-10-21 Impact factor: 15.419

3. A grossly warped nanographene and the consequences of multiple odd-membered-ring defects.

Authors: Katsuaki Kawasumi; Qianyan Zhang; Yasutomo Segawa; Lawrence T Scott; Kenichiro Itami
Journal: Nat Chem Date: 2013-07-14 Impact factor: 24.427

4. Palladium catalysed C-H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions.

Authors: Xavier Just-Baringo; Yuyoung Shin; Adyasha Panigrahi; Marco Zarattini; Vaiva Nagyte; Ling Zhao; Kostas Kostarelos; Cinzia Casiraghi; Igor Larrosa
Journal: Chem Sci Date: 2020-01-28 Impact factor: 9.825

Direct arylation of polycyclic aromatic hydrocarbons through palladium catalysis.

1. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules.

2. Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

3. A grossly warped nanographene and the consequences of multiple odd-membered-ring defects.

4. Palladium catalysed C-H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions.

5. One-shot K-region-selective annulative π-extension for nanographene synthesis and functionalization.

6. Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates.

7. Synthesis of extended polycyclic aromatic hydrocarbons by oxidative tandem spirocyclization and 1,2-aryl migration.

8. Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium-Catalyzed Arylation.

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

10. Synthesis of open-shell ladder π-systems by catalytic C-H annulation of diarylacetylenes.