Palladium-Catalyzed Dearomative Fluoroallylation of Pyrroles with <i>gem</i>-Difluorinated Cyclopropanes
We herein report the development of a novel Pd-catalyzed dearomative functionalization of pyrroles with <i>gem</i>-difluorinated cyclopropanes (<i>gem</i>-F<sub>2</sub>CPs). This dearomative/ring-opening strategy streamlines the diversity-oriented synthesis (DOS) of α-quaternary 2-fluoroallylic 2<i>H</i>-pyrroles with a broad scope and excellent functional group tolerance, which enables the efficient late-stage transformation of complex bioactive molecule-derived <i>gem</i>-F<sub>2</sub>CPs. Derivation of the resulting fluoroallylic 2<i>H</i>-pyrroles to different synthetically useful fluoroallylic 2<i>H</i>-pyrrole motifs demonstrated the synthetic value of this methodology.
Authors
- Long Gu (ORCID: https://orcid.org/0000-0002-5576-031X)
- Zhaodong Li (ORCID: https://orcid.org/0009-0001-6234-6774)
- Fajie Duan (ORCID: https://orcid.org/0000-0002-2151-0785)
- Wei Li (ORCID: https://orcid.org/0000-0001-7801-3643)
- Yue Zhang (ORCID: https://orcid.org/0000-0002-8173-9696)
- Zhengquan Su (ORCID: https://orcid.org/0000-0001-6324-6620)
- Zhipeng Zhao (ORCID: https://orcid.org/0000-0002-5546-7762)
- Jiafeng Ye
Institutions
- South China Agricultural University (CN)
- Nanjing University of Chinese Medicine (CN)
- Indiana University School of Medicine
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c00817
- Citations
- 6
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 4.74
Funders
- National Key Research and Development Program of China
- Basic and Applied Basic Research Foundation of Guangdong Province