Organic Letters· 2026Q1
Uracil-Thianthrenium Salts (Uracil-TT+BF4–) as a Coupling Partner in Sonogashira Cross-Coupling Reactions: Access to 5-Alkynyl Uracils and Synthetic Applications
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- Q1SCImago
- 2026year
Short summary
A new bench-stable reagent, uracil-thianthrenium tetrafluoroborate (Uracil-TT+BF4–), enables Sonogashira cross-coupling to selectively install alkyne groups at the C-5 position of uracils, yielding desired products in good to excellent yields.
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Key points
- A new uracil-thianthrenium salt (Uracil-TT+BF4–) was synthesized as a stable cross-coupling reagent.
- The reagent enables selective Sonogashira coupling at the C-5 position of uracils.
- The protocol tolerates a wide range of terminal alkynes and functional groups, yielding products in good to excellent yields.
- Recovered thianthrene byproduct can be reused to regenerate the uracil-TT+ reagent, promoting sustainability.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Cross-coupling reactions are powerful tools for forging two different organic fragments via formation of C–C or C–heteroatom bonds. Herein, we for the first time synthesize a bench-stable cross-coupling reagent, uracil-TT+BF4–, for Sonogashira-type reaction to install an alkyne functionality selectively at position C-5 of uracils. A series of terminal alkynes were tolerated well, affording the desired products in good to excellent yields. Moreover, mild conditions, low catalyst loading, a broad substrate scope, and excellent functional group tolerance are some notable features of the current protocol. Furthermore, byproduct thianthrene (TT) formed in this reaction has been recovered and reused for making the uracil-TT+ reagent, highlighting the sustainability of the method.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry