Recent Advances in Cross-Couplings of Functionalized Organozinc Reagents

Wei, Baosheng und Knochel, Paul (2021): Recent Advances in Cross-Couplings of Functionalized Organozinc Reagents. In: Synthesis-Stuttgart, Bd. 54, Nr. 2: S. 246-254

Abstract

Cross-couplings involving organozinc reagents usually require a Pd-catalyst (Negishi cross-coupling), however, uncatalyzed cross-couplings of zinc organometallics proceed well in the absence of transition-metal catalysts with reactive electrophiles such as benzal 1,1-diacetates, benzhydryl acetates, and iminium trifluoroacetates. Organozinc compounds also undergo C-N bond formation with O-benzoylhydroxylamines or organic azides in the presence of cobaltor iron-catalysts. Highly diastereoselective and enantioselective cross-couplings can be readily performed with room-temperature configurationally stable alkylzinc species, producing diastereoselectively and enantiomerically enriched products. Finally, highly regioselective magnesiations of functionalized arenes and heteroarenes undergo Negishi (after transmetalation with ZnCl2) or Cu-catalyzed cross-couplings.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0039-7881
• Sprache: Englisch