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Synfacts 2019; 15(11): 1285
DOI: 10.1055/s-0039-1690327
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

The Hiyama–Denmark Cross-Coupling

Contributor(s):
Mark Lautens
,
José F. Rodríguez
Denmark SE. * Sweis RF. University of Illinois, Urbana, USA
Fluoride-Free Cross-Coupling of Organosilanols.

J. Am. Chem. Soc. 2001;
123: 6439-6440
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Further Information

Publication History

Publication Date:
18 October 2019 (online)

 
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Key words

palladium catalysis - organosilanols - cross-coupling

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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