Phosphazene Base <i>t</i> ‐Bu‐P2‐Catalyzed Substitution Reactions of <i>para</i> ‐Hydroxybenzyl Alcohols
Abstract Herein, we report the substitution reactions of para ‐hydroxybenzyl alcohols catalyzed by the phosphazene base t ‐Bu‐P2. This system is compatible with substrates bearing various functionalities, including alkyl, methoxy, thiophenyl, halogen, ester, and amide moieties. Thiols, 1,3‐dicarbonyl compounds, and amines can be used as nucleophiles. Mechanistically, the reaction proceeds via E1cB elimination of the benzylic hydroxyl group from the phenoxide intermediate to generate a para ‐quinone methide intermediate, followed by nucleophilic 1,6‐addition.
Authors
- Yoshinori Kondo (ORCID: https://orcid.org/0000-0001-7171-7672)
- Masanori Shigeno (ORCID: https://orcid.org/0000-0002-9640-8283)
- Ozora Sasamoto (ORCID: https://orcid.org/0000-0001-5287-9940)
- Ken Osaka (ORCID: https://orcid.org/0000-0001-6885-9514)
- Toshinobu Korenaga (ORCID: https://orcid.org/0000-0002-9156-536X)
- Kazutoshi Hayashi
Institutions
- Iwate University (JP)
- Tohoku University (JP)
- Japan Science and Technology Agency (JP)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2025-05-22
- DOI
- https://doi.org/10.1002/ajoc.202500407
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Takeda Science Foundation
- Japan Science and Technology Corporation
- Precursory Research for Embryonic Science and Technology