10.1002/anie.202010737
Angewandte Chemie International Edition
COMMUNICATION
products.28 The strong coordination tendency of the vinylsilicon
unit towards the low-valent nickel might be crucial to forming
complex C.29 Alternatively, the nucleophilic substitution of in situ
generated R–M with Si–Cl may also result in the desired
product.30
[2] Some pioneering work: (a) M. Amatore, C. Gosmini, Angew. Chem. 2008,
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Scheme 8. Proposed mechanism.
In conclusion, we have developed the first cross-electrophile
C–Si coupling reaction. Although the mechanism requires further
investigation, this work has established a new platform for facile
and precise synthesis of organosilanes. The protocol is
distinguished by mild reaction conditions, broad substrate scope,
great functionality tolerance, and easy scalability. It thus
constitutes a new and complementary C–Si bond disconnection
strategy that is likely to find broad synthetic applications, because
of the ready availability of both coupling partners and the
widespread use of vinylsilanes in many fields. This work has
bridged the cross-electrophile coupling with organosilicon
chemistry. Therefore, we anticipate our method to be a starting
point for more useful discovery in these two areas. Work on the
detailed mechanism of this reaction, further expansion of the
scope of cross-electrophile silylation reactions, and the
application of the vinylsilanes are ongoing in our laboratory.
[5] Nucleophilic substitution of Si–Cl with R–MgX/Li is a classic and commonly
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Acknowledgements
We thank the National Natural Science Foundation of China for
financial support (21772072). We acknowledge the NMR facility
at SKLAOC, and Mr. Fengming Qi and Mr. Songqing Liu for their
expert assistance.
Author Contributions
† These authors contributed equally.
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Conflicts of Interest
The authors declare no conflicts of interest.
Keywords: organosilanes • vinylsilanes • cross-coupling •
reductive coupling • nickel
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