JACS Au· 2026Q1
Copper-Catalyzed 1,3-Propargyl Shift: Development of an Anionic Rearrangement of ortho -Metalated Aryl Propargyl Ethers
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- Q1SCImago
- 2026year
Short summary
A new copper-catalyzed anionic rearrangement allows propargyl ethers to shift a propargyl group from oxygen to an ortho-carbon on an aryl ring, creating hard-to-synthesize phenol derivatives.
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Key points
- Developed a novel anionic [1,3]-rearrangement of ortho-metalated aryl propargyl ethers.
- Copper(I) salt efficiently catalyzes the transfer of a propargyl group from oxygen to an ortho-carbon.
- Yields phenol derivatives with an ortho-propargyl group, a challenging synthetic target.
- The rearrangement is stereoretentive, allowing for chirality transfer in asymmetric synthesis.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract A novel anionic [1,3]-rearrangement of ortho-metalated aryl propargyl ethers was developed. A catalytic amount of copper(I) salt efficiently promotes the 1,3-shift of a propargyl group from an oxygen atom to a carbon atom in an aryl magnesium species, affording phenol derivatives having a propargyl group at the ortho position, which are otherwise difficult to synthesize. The [1,3]-rearrangement proceeds in a stereoretentive manner, thus enabling chirality transfer for asymmetric syntheses of enantio-enriched propargyl compounds. DFT calculations were conducted to elucidate the mechanism of the 1,3-propargyl shift.
The authors' abstract, as published at the source. JACS Au, 2026 · DOI ↗
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