ArticleChemical science2018
Selective oxymetalation of terminal alkynes
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Synthesis and Fluorescent Properties of Alkynylated 3‑Methylidenephthalides with Extended π‑Systems.ACS omega · 2025Article
- Total Synthesis of Ganoapplanin Enabled by a Radical Addition/Aldol Reaction Cascade.Journal of the American Chemical Society · 2024Article
- Carbometalation and Heterometalation of Carbon-Carbon Multiple-Bonds Using Group-13 Heavy Metals: Carbogallation, Carboindation, Heterogallation, and Heteroindation.Chemistry, an Asian journal · 2020Review
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The cyclization of heteroatom-containing alkynes with π acidic metal salts is an attractive method to prepare heterocycles because the starting materials are readily available and the organometallic compounds are useful synthetic intermediates. A new organometallic species in the heterocyclization provides an opportunity to synthesize heterocycles that are difficult to obtain. Herein, we describe a novel cyclic oxymetalation of 2-alkynylbenzoate with indium or gallium salts that proceeds with an unusual regioselectivity to give isocoumarins bearing a carbon-metal bond at the 4-position. This new type of metalated isocoumarin provided 3-unsubstituted isocoumarins that have seldom been investigated despite their important pharmacological properties. Indium and gallium salts showed high performance in the selective 6-
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Registered trials
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