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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.


 

Review

S. E. Denmark, R. F. Sweis Acc. Chem. Res. 2002, 35, 835–846.


 

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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