The Journal of Organic Chemistry· 2026Q2
Accessing Sterically Congested Benzannulated Cyclic Aryl Ethers via Photoredox Decarboxylative Giese-Type C2–C3 Bond Formation
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- 2026year
Short summary
A visible-light photocatalytic method enables the synthesis of sterically hindered five- to eight-membered oxygen heterocycles by forming a C2-C3 bond via decarboxylative Giese addition.
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Key points
- Visible-light photocatalysis drives the decarboxylation of α-aryloxy carboxylic acids.
- Intramolecular Giese addition of the resulting radicals forms C2-C3 bonds.
- Enables synthesis of sterically hindered five- to eight-membered oxygen heterocycles (2,3-dihydrobenzofurans, chromans, tetrahydrobenzo[b]oxepines, and tetrahydro-2H-benzo[b]oxocines).
- Mild reaction conditions ensure high chemoselectivity and functional group compatibility.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract The visible-light-driven photocatalytic decarboxylation of α-aryloxy carboxylic acids produces α-oxy carbon-centered radicals that undergo intramolecular Giese addition to form 2,3-dihydrobenzofurans, chromans, 2,3,4,5-tetrahydrobenzo[b]oxepines, and 3,4,5,6-tetrahydro-2H-benzo[b]oxocines. In contrast to the existing methods, this unconventional strategy for the construction of five-, six-, seven-, and eight-membered oxygen heterocycles via the formation of the C2–C3 bond enables the synthesis of sterically demanding O-heterocycles bearing multiple substituents at the C2 and C3 positions. The mild reaction conditions render these transformations highly chemoselective and compatible with various functional groups.
The authors' abstract, as published at the source. The Journal of Organic Chemistry, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry