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Peer-reviewedCC BYThe Journal of organic chemistry

Accessing Sterically Congested Benzannulated Cyclic Aryl Ethers via Photoredox Decarboxylative Giese-Type C2-C3 Bond Formation.

  • Igor Topalović1
  • Markus Lange1
  • Ivan Vilotijević1
  1. 1Institute for Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, 07743Jena, Germany.
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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.

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Cite

BibTeXRIS
BibTeX
@article{topalovic2026accessing,
  title = {{Accessing Sterically Congested Benzannulated Cyclic Aryl Ethers via Photoredox Decarboxylative Giese-Type C2-C3 Bond Formation.}},
  author = {Igor Topalović and Markus Lange and Ivan Vilotijević},
  journal = {The Journal of organic chemistry},
  year = {2026},
  month = sep,
  doi = {10.1021/acs.joc.6c01643},
  url = {https://europepmc.org/article/MED/42917441},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Accessing Sterically Congested Benzannulated Cyclic Aryl Ethers via Photoredox Decarboxylative Giese-Type C2-C3 Bond Formation.
AU  - Igor Topalović
AU  - Markus Lange
AU  - Ivan Vilotijević
PY  - 2026
DA  - 2026/09/01
JO  - The Journal of organic chemistry
DO  - 10.1021/acs.joc.6c01643
UR  - https://europepmc.org/article/MED/42917441
AB  - 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.
SN  - 0022-3263
SN  - 1520-6904
ER  -