SCF3‑Alkenes Unlocked: A Gateway via Cu(I)-Catalyzed Stereocontrolled Cross-Coupling
(2026) Organic Letters — Vol. 28, n° 11, p. 3565-3571 (2026)
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- Abstract
- The SCF3 group has emerged as a key motif in medicinal and agrochemical chemistry. While synthetic methods to access aryl, alkynyl, and alkyl SCF3-derivatives are well-established, access to stereocontrolled SCF3-disubstituted alkenes remains challenging, with existing methods falling short on selectivity and substrate scope. Here we report a versatile Cu(I)-catalyzed crosscoupling that unlocks modular, stereodefined access to (E)-, (Z)-, and (1,1′)-disubstituted SCF3-alkenes under mild, user-friendly conditions - breaking through key limitations of previous approaches. This scalable protocol exhibits broad functional group tolerance and handles complex, pharma- and agro-relevant substrates with ease. Moreover, the SCF3-alkenes serve as versatile platforms for selective postfunctionalization. Mechanistic evidence points to a two-electron pathway involving a hypervalent silicon intermediate, shedding light on this novel transformation.
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Salamone, L., Vanderbiest, X., & Riant, O. (2026). SCF3‑Alkenes Unlocked: A Gateway via Cu(I)-Catalyzed Stereocontrolled Cross-Coupling. Organic Letters, 28(11), 3565-3571. https://doi.org/10.1021/acs.orglett.6c00527 (Original work published 2026)