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Peer-reviewedCC BY-NC-ND 4.0JACS Au

Photocatalytic Two-Carbon Skeletal Expansion of Cyclic Alcohols to Cycloalkenes

  • Braja Kishor Paul1
  • Malekul Islam1
  • Fadil Faizal Mannighayil1
  • Suman De Sarkar1
  1. 1Indian Institute of Science Education and Research Kolkata , , , ,
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Abstract

A unified strategy for accessing substituted cycloalkenes via two-carbon ring expansion of cycloalkanols is described. Organophotocatalyzed oxidation of cycloalkanols, proceeding either via direct oxidation or via proton-coupled electron transfer (PCET), is sequentially coupled with intramolecular Wittig olefination. This process converts previously unexplored ketone intermediates into valuable cycloalkenes across a broad substrate scope and in high yields. The post-synthetic diversification of the products serves as a synthetic handle for downstream manipulations, thus offering opportunities to build up many complex molecular architectures. Combined experimental studies support a sequential mechanism involving radical ring fragmentation-addition followed by ionic Wittig olefination, affording the desired cycloalkene derivatives.

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Cite

BibTeXRIS
BibTeX
@article{paul2026photocatalytic,
  title = {{Photocatalytic Two-Carbon Skeletal Expansion of Cyclic Alcohols to Cycloalkenes}},
  author = {Braja Kishor Paul and Malekul Islam and Fadil Faizal Mannighayil and Suman De Sarkar},
  journal = {JACS Au},
  year = {2026},
  month = oct,
  doi = {10.1021/jacsau.6c01304},
  url = {https://pubs.acs.org/jaaucr/article/doi/10.1021/jacsau.6c01304/5456477/Photocatalytic-Two-Carbon-Skeletal-Expansion-of},
  note = {CC BY-NC-ND 4.0},
}
RIS
TY  - JOUR
TI  - Photocatalytic Two-Carbon Skeletal Expansion of Cyclic Alcohols to Cycloalkenes
AU  - Braja Kishor Paul
AU  - Malekul Islam
AU  - Fadil Faizal Mannighayil
AU  - Suman De Sarkar
PY  - 2026
DA  - 2026/10/22
JO  - JACS Au
DO  - 10.1021/jacsau.6c01304
UR  - https://pubs.acs.org/jaaucr/article/doi/10.1021/jacsau.6c01304/5456477/Photocatalytic-Two-Carbon-Skeletal-Expansion-of
AB  - A unified strategy for accessing substituted cycloalkenes via two-carbon ring expansion of cycloalkanols is described. Organophotocatalyzed oxidation of cycloalkanols, proceeding either via direct oxidation or via proton-coupled electron transfer (PCET), is sequentially coupled with intramolecular Wittig olefination. This process converts previously unexplored ketone intermediates into valuable cycloalkenes across a broad substrate scope and in high yields. The post-synthetic diversification of the products serves as a synthetic handle for downstream manipulations, thus offering opportunities to build up many complex molecular architectures. Combined experimental studies support a sequential mechanism involving radical ring fragmentation-addition followed by ionic Wittig olefination, affording the desired cycloalkene derivatives.
SN  - 2691-3704
ER  -