Synfacts 2020; 16(12): 1451
DOI: 10.1055/s-0040-1719506
Metals in Synthesis

Cross-Coupling of Organosilanes with Organic Halides Mediated by Palladium Catalyst and TASF

Rezensent(en):
Paul Knochel
,
Dimitrije Djukanovic
Hatanaka Y, Hiyama T. * Sagami Chemical Research Center, Sagamihara, Japan
Cross-Coupling of Organosilanes with Organic Halides Mediated by Palladium Catalyst and Tris(diethlamino)sulfonium Difluorotrimethylsilicate.

J. Org. Chem. 1988;
53: 918-920
DOI: 10.1021/jo00239a056.
 

Significance

In 1988, the authors reported a catalytic coupling of simple trimethylsilanes and organohalides in a process that is now known as Hiyama cross-coupling. Organosilanes are stable, easy to handle coupling partners that have low toxicity and good solubility. In addition to trialkylsilanes, trialkoxysilanes and fluoroalkylsilanes are also competent coupling partners. However, a stable C–Si bond requires activation, which is most commonly performed by using a F source.


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Comment

In this first report coupling proceeded under relatively mild conditions and sensitive products were obtained. However, the scope of organosilanes was very limited. Today, many protocols exist for coupling of organosilanes. Those that are fluoride-free are especially useful and desirable. The commercial availability of organosilanes remains a limiting factor in the widespread use of Hiyama coupling.

Review: Y. Nakao, T. Hiyama Chem. Soc. Rev. 2011, 40, 4893–4901.


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Die Autoren geben an, dass kein Interessenkonflikt besteht.


Publikationsverlauf

Publikationsdatum:
17. November 2020 (online)

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