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 cross-coupling 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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L Salamone
Xavier Vanderbiest
Olivier Riant
Organic Letters
UCLouvain
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Salamone et al. (Wed,) studied this question.
www.synapsesocial.com/papers/69abc0b85af8044f7a4e95b0 — DOI: https://doi.org/10.1021/acs.orglett.6c00527
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