A Catalytic Synthesis of Thiosilanes and Silthianes:  Palladium Nanoparticle-Mediated Cross-Coupling of Silanes with Thio Phenyl and Thio Vinyl Ethers through Selective Carbon−Sulfur Bond Activation

Palladium nanoparticles generated in situ from N,N-dimethyl-acetamide (DMA) solutions of PdX2 (X = Cl-, OAc-, OCOCF3 -) or Pd2(dba)3 by reduction with alkyl silanes R3SiH (R = Me, Et, i-Pr, t-Bu) are selective catalysts for the cross-coupling of the silanes R3SiH with phenyl and vinyl thioethers for...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2004-06, Vol.126 (23), p.7386-7392
Main Authors: Chung, Mee-Kyung, Schlaf, Marcel
Format: Article
Language:English
Subjects:
Carbon - chemistry
Catalysis
Chemistry
Colloids
Exact sciences and technology
Glucose - chemistry
Microscopy, Scanning Tunneling
Molecular Structure
Organic chemistry
Palladium - chemistry
Silanes - chemical synthesis
Silanes - chemistry
Sulfides - chemistry
Sulfur - chemistry
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Summary:Palladium nanoparticles generated in situ from N,N-dimethyl-acetamide (DMA) solutions of PdX2 (X = Cl-, OAc-, OCOCF3 -) or Pd2(dba)3 by reduction with alkyl silanes R3SiH (R = Me, Et, i-Pr, t-Bu) are selective catalysts for the cross-coupling of the silanes R3SiH with phenyl and vinyl thioethers forming the corresponding thiosilanes and silthianes in high yields and under mild conditions. The method is applicable to phenyl thioglycosides, giving access to thiosilyl glycosides a new class of sugar derivatives.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja049386u