Recent Advances in Cross-Couplings of Functionalized Organozinc Reagents

Wei, Baosheng and Knochel, Paul (2021): Recent Advances in Cross-Couplings of Functionalized Organozinc Reagents. In: Synthesis-Stuttgart, Vol. 54, No. 2: pp. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0039-7881
• Language: English