# Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides

**Authors:** Andrea Messina, Filippo Monticelli, Tiziano Miroglio, Anna Gagliardi, Igor Viviani, Luca Banfi, Renata Riva, Lisa Moni, Andrea Basso, Chiara Lambruschini

PMC · DOI: 10.3390/molecules30122584 · Molecules · 2025-06-13

## TL;DR

This paper presents a new method using light-activated palladium to insert isocyanides into inactive alkyl iodides, forming amides efficiently.

## Contribution

A novel photoexcited palladium-catalyzed method for isocyanide insertion into inactivated alkyl iodides is introduced.

## Key findings

- The method produces substituted secondary amides in good to high yields.
- 4-(N,N-dimethylamino)pyridine is hypothesized to play a key role in the reaction mechanism.

## Abstract

Isocyanides insertions represent an important transformation in the palladium-catalyzed reactions landscape. However, one of their most significant limitations is in the use of inactivated alkyl electrophiles. Palladium photocatalysis has been proven as a solid tool for the generation of alkyl radicals from alkyl halides, which may engage in subsequent transformations with a variety of reaction partners, closing the catalytic cycle. Herein, we report the mild three-component isocyanide insertions into inactivated alkyl iodides mediated by the catalytic activity of a photoexcited palladium complex. We investigated the scope of the reaction obtaining differently substituted secondary amides in good to high yields. We also investigated the mechanism, hypothesizing a key role of 4-(N,N-dimethylamino)pyridine in the outcome of the reaction.

## Linked entities

- **Chemicals:** 4-(N,N-dimethylamino)pyridine (PubChem CID 14284)

## Full-text entities

- **Chemicals:** Alkyl Iodides (-), Palladium (MESH:D010165), 4-(N,N-dimethylamino)pyridine (MESH:C578863), amides (MESH:D000577), Isocyanide (MESH:D003486)

## Full text

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## Figures

8 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12196398/full.md

## References

27 references — full list in the complete paper: https://tomesphere.com/paper/PMC12196398/full.md

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Source: https://tomesphere.com/paper/PMC12196398