# Advancing total synthesis through the Stille cross-coupling: recent innovations and case studies

**Authors:** Elaheh Hashemi, Mohammad Teimoury

PMC · DOI: 10.1039/d5ra06557g · RSC Advances · 2026-01-12

## TL;DR

The Stille reaction is a key tool in making complex natural products and pharmaceuticals through efficient chemical coupling.

## Contribution

This review highlights recent innovations in Stille cross-coupling, including eco-friendly protocols and improved catalytic strategies.

## Key findings

- The Stille reaction remains vital for constructing complex molecules due to its versatility and functional group tolerance.
- Recent advancements address tin toxicity and improve the sustainability of the reaction.
- The reaction is effective in both intermolecular and intramolecular contexts in organic synthesis.

## Abstract

The Stille reaction, a pivotal palladium-catalyzed cross-coupling, continues to drive advancements in the total synthesis of highly complex natural products, pharmaceuticals, and functional materials. Originating from John K. Stille's foundational work, this method has evolved through innovations in catalysis, ligand design, and eco-friendly protocols to address challenges like tin toxicity. This review highlights its application in constructing complex molecules and emphasizes advancements in bond-forming strategies. The reaction's versatility in both intermolecular and intramolecular contexts, coupled with its functional group tolerance, underscores its enduring relevance in modern organic synthesis of naural products.

The Stille reaction, a pivotal palladium-catalyzed cross-coupling, continues to drive advancements in the total synthesis of highly complex natural products, pharmaceuticals, and functional materials.

## Full-text entities

- **Chemicals:** tin toxicity (-), palladium (MESH:D010165)

## Full text

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## Figures

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## References

98 references — full list in the complete paper: https://tomesphere.com/paper/PMC12794845/full.md

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Source: https://tomesphere.com/paper/PMC12794845