Umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones for the regiodivergent synthesis of disubstituted catechols
Abstract The umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones 1 with PhI(OCOCF3)2 achieved the migration into the more electron-rich C3 position, providing exclusively 3,4-disubstituted catechols 3. Acid-induced rearrangement of 1 produced 4,5-disubstituted catechols 2. These two reactions enabled the highly selective production of two regioisomers of disubstituted catechols, especially biaryls containing catechol moieties, from the common intermediates 1.
Authors
- Yoshinari Sawama (ORCID: https://orcid.org/0000-0002-9923-2412)
- Masatoshi Togami
- Kenzo Yahata (ORCID: https://orcid.org/0000-0002-6991-9221)
- Ahmed A. B. Mohamed (ORCID: https://orcid.org/0000-0003-3912-1021)
- Kyohei Kanomata (ORCID: https://orcid.org/0000-0002-2251-4665)
- Shuji Akai (ORCID: https://orcid.org/0000-0001-9149-8745)
- Ryunosuke Akazawa
- Kohei Miyagaki
Institutions
- Mansoura University (EG)
- The University of Osaka (JP)
Publication Details
- Journal
- Bulletin of the Chemical Society of Japan
- Published
- 2024-10-24
- DOI
- https://doi.org/10.1093/bulcsj/uoae111
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Japan Agency for Medical Research and Development