Naphthalene Hydrodearomatization via Controllable Photocatalytic Hydroboration
The photocatalytic dearomative 1,4-hydroboration of naphthalenes with an N-heterocyclic carbene borane (NHC-BH<sub>3</sub>) complex was reported herein with controllable regioselectivity and chemoselectivity. This protocol yielded a wide range of naphthalene derivatives bearing various functional groups, notably bioactive compounds. Hydroboration occurred through the cooperation of photoredox and hydrogen atom transfer via boryl radical addition to naphthalene and further selective protonation. Notably, tuning the conditions could lead to further hydrogenation of the tetrahydroboration products. Mechanistic studies, including experimental and computational studies, elucidated the mechanism for the regioselectivity.
Authors
- Wengang Xu (ORCID: https://orcid.org/0000-0002-8468-8468)
- Fengyu Ma
- Mingbo Wu (ORCID: https://orcid.org/0000-0003-0048-778X)
- Feng‐Lian Zhang (ORCID: https://orcid.org/0000-0003-3806-2269)
- Juan Tao
- Qiao Zhang (ORCID: https://orcid.org/0000-0001-9682-3295)
- Yuqi Wang (ORCID: https://orcid.org/0000-0002-9793-6002)
- Mingrui Liu (ORCID: https://orcid.org/0000-0002-6499-7212)
Institutions
- University of Science and Technology of China (CN)
- China University of Petroleum, East China (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-21
- DOI
- https://doi.org/10.1021/acs.joc.4c02732
- Citations
- 1
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Natural Science Foundation of Shandong Province
- University of Science and Technology of China
- Major Scientific and Technological Innovation Project of Shandong Province