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DOI: 10.1055/a-1589-0150
Recent Advances in Cross-Couplings of Functionalized Organozinc Reagents
We thank the Deutsche Forschungsgemeinschaft (DFG) and the Cluster of Excellence e-conversion for financial support.
Dedicated to the memory of Victor Snieckus, a pioneer of organometallic chemistry and missing friend
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 cobalt- or 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.
1 Introduction
2 Uncatalyzed Cross-Couplings of Organozinc Reagents with Highly Electrophilic Partners
3 Iron- and Cobalt-Catalyzed Aminations using Organozinc Reagents
4 Stereo- and Regioselective Cross-Couplings of Organozinc Reagents
5 Conclusion
Key words
cross-coupling - organozinc reagents - carbon–carbon bond formation - carbon–nitrogen bond formation - amination - diastereoselective reaction - enantioselective reactionPublication History
Received: 29 July 2021
Accepted after revision: 16 August 2021
Accepted Manuscript online:
16 August 2021
Article published online:
12 October 2021
© 2021. Thieme. All rights reserved
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