Nickel-Catalyzed Stereoconvergent C(sp<sup>2</sup>)–F Alkenylation of Monofluoroalkenes
The stereoconvergent synthesis of a single stereoisomer from <i>E</i>/<i>Z</i>-olefin mixtures remains one of the foremost challenges in organic synthesis. Herein, we describe a nickel-catalyzed stereoconvergent cross-coupling between <i>E</i>- and <i>Z</i>-mixed monofluoroalkenes and alkenyl electrophiles, which allows the construction of C(sp<sup>2</sup>)-C(sp<sup>2</sup>) bonds. This defluorinative transformation offers facile access to various 1,3-dienes with <i>E</i>-selectivity and good functional group tolerance. Preliminary mechanistic studies indicate that the reaction most likely proceeds through a migratory insertion/β-F elimination/isomerization process.
Authors
- Dayong Shi (ORCID: https://orcid.org/0000-0001-8941-5285)
- Ruihua Liu (ORCID: https://orcid.org/0000-0002-2517-1581)
- Leifeng Yuan (ORCID: https://orcid.org/0009-0005-5082-3712)
- Wenlong Shan
- Cong Shi (ORCID: https://orcid.org/0009-0000-5681-3834)
- Hongyun Qin (ORCID: https://orcid.org/0000-0003-4531-8330)
- Zemin Wang (ORCID: https://orcid.org/0000-0002-2660-3876)
- Jiashu Chen (ORCID: https://orcid.org/0000-0003-3222-1628)
- Xiaowei Li (ORCID: https://orcid.org/0000-0001-7586-2850)
- Wenli Zhuang
- Nan Zhou
- Xiangqian Li (ORCID: https://orcid.org/0000-0002-8649-3728)
Institutions
- Shandong University (CN)
- Qingdao National Laboratory for Marine Science and Technology (CN)
- State Key Laboratory of Microbial Technology
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-27
- DOI
- https://doi.org/10.1021/acs.orglett.4c03107
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.21
Funders
- Natural Science Foundation of Shandong Province
- Key Technology Research and Development Program of Shandong
- Science and Technology Development Plan of Shandong Province
- National Key Research and Development Program of China