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Palladium-catalyzed cyanation and alkynylation of allylic gem-difluorides via Hiyama-type coupling.

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Název: Palladium-catalyzed cyanation and alkynylation of allylic gem-difluorides via Hiyama-type coupling.
Autoři: Miao, Jia-cheng, Tang, Lu-ning, Wang, Yi-bin, Kong, Xian-qiang, Chen, Ming
Zdroj: Chemical Communications; 11/11/2025, Vol. 61 Issue 87, p17025-17028, 4p
Témata: PALLADIUM catalysts, CYANATES, ORGANOFLUORINE compounds, PERFLUORO compounds, FUNCTIONAL groups, ALKYLATION
Abstrakt: We report a palladium-catalyzed Hiyama-type defluorinative cross-coupling of allylic gem-difluorides with trimethylsilyl cyanide and silylalkynes via selective C–F bond activation. The reaction involves oxidative addition, Si–F-assisted transmetalation, and reductive elimination, enabling efficient construction of C(sp3)–CN and C(sp3)–C(sp) bonds under mild, additive-free conditions. It features broad substrate scope, excellent functional group tolerance, and high regio- and Z-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. [ABSTRACT FROM AUTHOR]
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Abstrakt:We report a palladium-catalyzed Hiyama-type defluorinative cross-coupling of allylic gem-difluorides with trimethylsilyl cyanide and silylalkynes via 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 Z-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. [ABSTRACT FROM AUTHOR]
ISSN:13597345
DOI:10.1039/d5cc05064b