Palladium-catalyzed cyanation and alkynylation of allylic <i>gem</i> -difluorides <i>via</i> Hiyama-type coupling
We report a palladium-catalyzed Hiyama-type defluorinative cross-coupling of allylic gem-difluorides with trimethylsilyl cyanide and silylalkynes <i>via</i> selective C-F bond activation. The reaction involves oxidative addition, Si-F-assisted transmetalation, and reductive elimination, enabling efficient construction of C(sp<sup>3</sup>)-CN and C(sp<sup>3</sup>)-C(sp) bonds under mild, additive-free conditions. It features broad substrate scope, excellent functional group tolerance, and high regio- and <i>Z</i>-selectivity, affording diverse monofluorinated alkenes in good to excellent yields. The resulting fluoroalkenes serve as versatile intermediates for downstream functionalization, highlighting the synthetic utility of this Si-F-driven platform.
Authors
- Luning Tang
- Xianqiang Kong (ORCID: https://orcid.org/0000-0002-5621-0416)
- Ming Chen (ORCID: https://orcid.org/0000-0003-4957-2934)
- Yibin Wang (ORCID: https://orcid.org/0009-0005-0436-9432)
- Jing Miao (ORCID: https://orcid.org/0000-0003-4436-2823)
Institutions
- Changzhou Institute of Technology (CN)
- Changzhou University (CN)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc05064b
- Citations
- 2
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.58