C–F Activation for C(sp2)–C(sp3) Cross-Coupling by a Secondary Phosphine Oxide (SPO)-Nickel Complex

A secondary phosphine oxide (SPO)-nickel catalyst allowed the activation of otherwise inert C–F bonds of unactivated arenes in terms of challenging couplings with primary and secondary alkyl Grignard reagents. The C–F activation is characterized by mild reaction conditions and high levels of branche...

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Bibliographic Details
Published in:Organic letters 2020-09, Vol.22 (17), p.7034-7040
Main Authors: Müller, Valentin, Ghorai, Debasish, Capdevila, Lorena, Messinis, Antonis M, Ribas, Xavi, Ackermann, Lutz
Format: Article
Language:English
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Summary:A secondary phosphine oxide (SPO)-nickel catalyst allowed the activation of otherwise inert C–F bonds of unactivated arenes in terms of challenging couplings with primary and secondary alkyl Grignard reagents. The C–F activation is characterized by mild reaction conditions and high levels of branched selectivity. Electron-rich and electron-deficient arenes were suitable electrophiles for this transformation. In addition, this strategy also proved suitable to heterocycles and for the activation of C–O bonds under slightly modified conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02609