Pd-Catalyzed Annulation of Aryl Iodides with Ynamides for the Synthesis of 9-Aminophenanthrenes: Regioselectivity in Reductive Elimination of Pallada(IV)cycle

This work describes an efficient Pd-catalyzed three-component annulation process of aryl iodides and ynamides. A wide variety of 9-aminophenanthrenes bearing various functional groups can be obtained in up to 94% yield. The reaction likely proceeds via a 3-amino-substituted pallada(IV)cycle through sequential reaction processes. It appears that the formation of the aryl-vinyl bond is preferred over the aryl-aryl bond during the reductive elimination of the pallada(IV)cycle.

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Publication Details

Journal
Organic Letters
Published
2026-03-28
DOI
https://doi.org/10.1021/acs.orglett.6c00735
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Pd-Catalyzed Annulation of Aryl Iodides with Ynamides for the Synthesis of 9-Aminophenanthrenes: Regioselectivity in Reductive Elimination of Pallada(IV)cycle

Huiying Hong, Wei’ao Liu, Xi Zhang, Yian Shi et al.
Organic Letters
Catalytic Alkyne Reactions
article

Pd-Catalyzed Annulation of Aryl Iodides with Ynamides for the Synthesis of 9-Aminophenanthrenes: Regioselectivity in Reductive Elimination of Pallada(IV)cycle

Huiying Hong, Wei’ao Liu, Xi Zhang, Yian Shi, Jianjun Wang
article en

Abstract

This work describes an efficient Pd-catalyzed three-component annulation process of aryl iodides and ynamides. A wide variety of 9-aminophenanthrenes bearing various functional groups can be obtained in up to 94% yield. The reaction likely proceeds via a 3-amino-substituted pallada(IV)cycle through sequential reaction processes. It appears that the formation of the aryl-vinyl bond is preferred over the aryl-aryl bond during the reductive elimination of the pallada(IV)cycle.

Organic Letters
Catalytic Materials (United States) (US), Changzhou University (CN)
Openalex Percentile: Top 4%
Catalytic Alkyne Reactions
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