A Palladium-Catalyzed Cascade Process of 1,3-Enynes and Imines to Construct Multisubstituted Pyrrole Derivatives

A palladium-catalyzed cascade reaction of 1,3-enynes and aldimines to efficiently access multisubstituted pyrroles is reported, proceeding in a Pd(0) π-Lewis base-mediated vinylogous addition, intramolecular central carbon <i>N</i>-allylation of the resultant π-allylpalladium species, protonation, β-H elimination, and isomerization sequence. In addition, benzosultam-fused dihydropyrroles, bearing a quaternary stereogenic center and an <i>exo</i>-cyclic double bond, are similarly furnished by using the related ketimines.

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Publication Details

Journal
Organic Letters
Published
2025-12-03
DOI
https://doi.org/10.1021/acs.orglett.5c04542
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

A Palladium-Catalyzed Cascade Process of 1,3-Enynes and Imines to Construct Multisubstituted Pyrrole Derivatives

Tianying Zhang, Wei Du, Ze-Liang He, Zhichao Chen et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

A Palladium-Catalyzed Cascade Process of 1,3-Enynes and Imines to Construct Multisubstituted Pyrrole Derivatives

Tianying Zhang, Wei Du, Ze-Liang He, Zhichao Chen, Ying‐Chun Chen, Bao-Rui Kong
article en

Abstract

A palladium-catalyzed cascade reaction of 1,3-enynes and aldimines to efficiently access multisubstituted pyrroles is reported, proceeding in a Pd(0) π-Lewis base-mediated vinylogous addition, intramolecular central carbon <i>N</i>-allylation of the resultant π-allylpalladium species, protonation, β-H elimination, and isomerization sequence. In addition, benzosultam-fused dihydropyrroles, bearing a quaternary stereogenic center and an <i>exo</i>-cyclic double bond, are similarly furnished by using the related ketimines.

Organic LettersVol. 27(50)
Sichuan University (CN)
Openalex Percentile: Top 71%
Catalytic C–H Functionalization Methods
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