Dialkylation of 1,3-Dienes with Aldehydes and Cyclopropanols toward Homoallylic Alcohols by Dual Photoredox and Chromium Catalysis
A visible-light-induced three-component coupling of aldehydes, 1,3-dienes, and cyclopropyl alcohols using dual photoredox and chromium catalysis is herein described. This efficient protocol achieves the dialkylation of 1,3-dienes toward 1,4-disubstituted homoallylic alcohols in moderate to good yields with excellent regioselectivity, featuring mild reaction conditions, good functional group tolerance, and gram-scale synthesis. Mechanistic study suggests that photoinduced sequential ring opening of cyclopropyl alcohol and radical and nucleophilic cascade addition are involved in the catalytic cycle.
Authors
- Zheng Fang (ORCID: https://orcid.org/0000-0002-3209-4713)
- Caipeng Wang
- Gaochen Xu
- Pei Guan
- Jindian Duan (ORCID: https://orcid.org/0000-0002-8378-8651)
- Kai Guo (ORCID: https://orcid.org/0000-0002-0013-3263)
- Delong Ma (ORCID: https://orcid.org/0000-0002-5669-369X)
- Lu Deng (ORCID: https://orcid.org/0000-0002-3026-4205)
- Yan Meng (ORCID: https://orcid.org/0009-0001-0185-4193)
Institutions
- Nanjing Tech University (CN)
- Luye Pharma (China) (CN)
- Pharmaceutical Biotechnology (Czechia) (CZ)
- Zhejiang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c00975
- Citations
- 6
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- Key Technology Research and Development Program of Shandong
- National Key Research and Development Program of China