Annulation of Phthalic Anhydrides with 2-Arylbenzimidazoles toward Phenanthridine-Fused Heterocycles: TBAI-Promoted Palladium Catalysis

A palladium/PPh<sub>3</sub>/TBAI catalyzed reaction has been developed, enabling sequential decarbonylation/decarboxylation/C-N and C-H bond formation within a single synthetic step. This innovative methodology features annulation of phthalic anhydrides with 2-arylbenzimidazoles, with TBAI serving as a vital iodide source that enhances the reactivity of the Pd(OAc)<sub>2</sub>/PPh<sub>3</sub> catalytic system. Notably, the incorporation of phthalic anhydride not only streamlines the synthesis but also supports environmentally friendly practices by minimizing waste and lessening reliance on hazardous substances typically associated with conventional arylation techniques.

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Publication Details

Journal
Organic Letters
Published
2025-10-22
DOI
https://doi.org/10.1021/acs.orglett.5c03207
Citations
1
Primary Topic
Chemical synthesis and alkaloids
Type
article
Field-Weighted Citation Impact
0.94
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article

Annulation of Phthalic Anhydrides with 2-Arylbenzimidazoles toward Phenanthridine-Fused Heterocycles: TBAI-Promoted Palladium Catalysis

Farnaz Jafarpour, Nafiseh Zarif Karimi
1 citations
Organic Letters
Chemical synthesis and alkaloids
0.94
article

Annulation of Phthalic Anhydrides with 2-Arylbenzimidazoles toward Phenanthridine-Fused Heterocycles: TBAI-Promoted Palladium Catalysis

Farnaz Jafarpour, Nafiseh Zarif Karimi
article en
1 citations

Abstract

A palladium/PPh<sub>3</sub>/TBAI catalyzed reaction has been developed, enabling sequential decarbonylation/decarboxylation/C-N and C-H bond formation within a single synthetic step. This innovative methodology features annulation of phthalic anhydrides with 2-arylbenzimidazoles, with TBAI serving as a vital iodide source that enhances the reactivity of the Pd(OAc)<sub>2</sub>/PPh<sub>3</sub> catalytic system. Notably, the incorporation of phthalic anhydride not only streamlines the synthesis but also supports environmentally friendly practices by minimizing waste and lessening reliance on hazardous substances typically associated with conventional arylation techniques.

Organic LettersVol. 27(43)
University of Tehran (IR)
Openalex Percentile: Top 20%
Chemical synthesis and alkaloids
0.94
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