ArticleNature communications2022
Diverse synthesis of C2-linked functionalized molecules via molecular glue strategy with acetylene.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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Who cites it
8 citing papers in PubMed.
- Metal-Catalyzed Hydrogen Atom Transfer (MHAT) Hydroalkylation with Electron-Deficient Alkynes.Organic letters · 2024Article
- Three-Component Gold(I)-Catalyzed Alkoxyvinylation.Organic letters · 2024Article
- Programmable synthesis of difluorinated hydrocarbons from alkenes through a photocatalytic linchpin strategy.Chemical science · 2023Article
- Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas.ACS catalysis · 2023Article
- A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction.Molecules (Basel, Switzerland) · 2023Article
- Synthesis of vinyl-substituted alcohols using acetylene as a C2 building block.Chemical science · 2023Article
- Thiol-Yne click chemistry of acetylene-enabled macrocyclization.Nature communications · 2022Article
- Cu-catalyzed carboboration of acetylene with Michael acceptors.Chemical science · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
As the simplest alkyne and an abundant chemical feedstock, acetylene is an ideal two-carbon building block. However, in contrast to substituted alkynes, catalytic methods to incorporate acetylene into fine chemicals are quite limited. Herein, we developed a photoredox-catalyzed synthetic protocol for diverse C2-linked molecules via a molecular glue strategy using gaseous acetylene under mild conditions. Initiated by addition of an acyl radical to acetylene, two cascade transformations follow. One involves a double addition for the formation of 1,4-diketones and the other where the intermediate vinyl ketone is intercepted by a radical formed from a heterocycle. In addition to making two new C-C bonds, two C-H bonds are also created in two mechanistically distinct ways: one via a C-H abstraction and the other via protonation. This system offers a reliable and safe way to incorporate gaseous acetylene into fine chemicals and expands the utility of acetylene in organic synthesis.
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Registered trials
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