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Synfacts 2019; 15(11): 1285
DOI: 10.1055/s-0039-1690327
DOI: 10.1055/s-0039-1690327
Metals in Synthesis
The Hiyama–Denmark Cross-Coupling
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Oktober 2019 (online)
![](https://www.thieme-connect.de/media/synfacts/201911/i_l135_s1_10-1055_s-0039-1690327.gif)
Significance
The authors reported a fluoride-free palladium-catalyzed cross-coupling of organosilanols with iodoarenes. Previous conditions for palladium-catalyzed cross-coupling of organosilanes required high temperatures and long reaction times.
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Review
S. E. Denmark, R. F. Sweis Acc. Chem. Res. 2002, 35, 835–846.
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Comment
Various iodoarenes reacted with an organosilanol to provide the cross-coupled products in high yields. The authors propose that a second molecule of silyloxide binds to the arylpalladium silyloxide to generate a pentacoordinate silicon intermediate, which can undergo a facile transmetalation.
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![](https://www.thieme-connect.de/media/synfacts/201911/i_l135_s1_10-1055_s-0039-1690327.gif)