Outcompeting hydrofunctionalization: Asymmetric remote substitution of alkynes.

Yi-Xiao Shen, Chao Ma, Guo-Qiang Lin, Zhi-Tao He

Abstract read

In one paragraph

Article in Science advances, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

–field-weighted citation impact

1 · What the graph read from it

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3 · Its place in the literature

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1 citing paper in PubMed.

Alkyne migratory functionalization via C(spNature communications · 2026
Article

4 · The record

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5 · Who and what money

Authors and funding

4 authors.

Yi-Xiao ShenState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.ORCID 0009-0008-3429-404X

Chao MaState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.

Guo-Qiang LinState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.ORCID 0000-0002-8209-5263

Zhi-Tao HeState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.ORCID 0000-0003-2375-9557

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Propargylic substitution is a broadly studied basic reaction but requires a vicinal leaving group in the alkyne substrate. Here, we describe the first asymmetric remote substitution of alkynes bearing a linear alkyl-linked remote leaving group via synergistic Pd/amine catalysis. A set of modified diamine organocatalysts guarantees the high regio-, geometry- and enantioselectivity of the remote coupling between alkynes and aldehydes, during which conventionally more competitive hydrofunctionalization process is completely inhibited. Scale-up test and various derivatizations show the reliability and value of the protocol. Mechanistic studies suggest that the formation of crucial 1,3-diene intermediate from alkyne and a complex redox pathway of Pd metal are involved in the catalytic cycle.

Identifiers

PMID41370389

DOI10.1126/sciadv.aeb0726

PMCPMC12694001

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