Palladium-Catalyzed Cyclization and Direct Arylation of 1-[2-(2,2-Dibromoethenyl)phenyl]-1<i>H</i>-pyrrole with Allenes

A novel and efficient palladium-catalyzed highly regioselective reaction of 1-[2-(2,2-dibromoethenyl)phenyl]-1<i>H</i>-pyrrole with allenes was realized to synthesize pyrrolo[1,2-<i>a</i>]quinolones. The tandem process involves intermolecular cyclization and intramolecular direct arylation, leading to the formation three new C-C bonds and two new rings. Notably, this transformation exhibits broad substrate scope and high functional group tolerance.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-10-09
DOI
https://doi.org/10.1021/acs.joc.4c00971
Citations
3
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.75

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article

Palladium-Catalyzed Cyclization and Direct Arylation of 1-[2-(2,2-Dibromoethenyl)phenyl]-1H-pyrrole with Allenes

Ping‐Xin Zhou, Xinqiang Tan, Ying‐Ying Kong, Zicheng Wang et al.
3 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.75
article

Palladium-Catalyzed Cyclization and Direct Arylation of 1-[2-(2,2-Dibromoethenyl)phenyl]-1H-pyrrole with Allenes

Ping‐Xin Zhou, Xinqiang Tan, Ying‐Ying Kong, Zicheng Wang, Xu Liu, Yu-Ji Wu, Meng-Yue Chen, Wang Feng, Shuai Wang, Yong‐Min Liang
article en
3 citations

Abstract

A novel and efficient palladium-catalyzed highly regioselective reaction of 1-[2-(2,2-dibromoethenyl)phenyl]-1<i>H</i>-pyrrole with allenes was realized to synthesize pyrrolo[1,2-<i>a</i>]quinolones. The tandem process involves intermolecular cyclization and intramolecular direct arylation, leading to the formation three new C-C bonds and two new rings. Notably, this transformation exhibits broad substrate scope and high functional group tolerance.

The Journal of Organic ChemistryVol. 89(20)
Lanzhou University (CN), Henan Medical University (CN)
Natural Science Foundation of Henan Province, Henan Provincial Science and Technology Research Project
Openalex Percentile: Top 32%
Catalytic C–H Functionalization Methods
0.75
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