A ligand-controlled regiodivergent three-component Heck-Tsuji reaction utilizing umpolung hydrazones enabled by palladium catalysis.

Evan F W Chen, Ruofei Cheng, Faraz Alaghemand, Rustam Z Khaliullin, Chao-Jun Li

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Article in Nature communications, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

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5 authors.

Evan F W Chen *Department of Chemistry, and FRQNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, QC, Canada.

Ruofei Cheng *Department of Chemistry, and FRQNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, QC, Canada.

Faraz AlaghemandDepartment of Chemistry, McGill University, Montreal, QC, Canada.ORCID http://orcid.org/0009-0002-6951-3544

Rustam Z KhaliullinDepartment of Chemistry, McGill University, Montreal, QC, Canada. rustam.khaliullin@mcgill.ca.ORCID http://orcid.org/0000-0002-9073-6753

Chao-Jun LiDepartment of Chemistry, and FRQNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, QC, Canada. cj.li@mcgill.ca.ORCID http://orcid.org/0000-0002-3859-8824

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Developing sustainable, selective strategies for the multicomponent functionalization of allenes remains an ongoing challenge in synthetic chemistry. We report a ligand-controlled, regiodivergent palladium-catalyzed three-component Heck-Tsuji reaction of allenes, aryl iodides, and umpolung hydrazones. Leveraging the umpolung reactivity of hydrazones as sustainable carbanion surrogates enables the direct arylalkylation of allenes, forming two C-C bonds in a single step. The ligand environment governs reaction outcomes, switching selectivity between branched and linear adducts using simple, commercially available ligands. This method tolerates a wide range of aryl, heteroaryl, and alkyl substrates, operates under mild conditions, and is amenable to late-stage diversification of complex molecules. Computational studies suggest a plausible explanation for the mechanistic basis of the ligand-dependent regioselectivity, providing reasonable insights for design of divergent Pd-catalyzed multicomponent coupling reactions.

Identifiers

PMID42754550

DOI10.1038/s41467-026-76749-0

PMCPMC13586255

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.