Rhodium(I)-Catalyzed Addition of Arylboronic Acids to (Benzyl-/Arylsulfonyl)acetonitriles: Efficient Synthesis of (Z)-β-Sulfonylvinylamines and β-Keto Sulfones

An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl sub...

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Bibliographic Details
Published in:Organic letters 2011-01, Vol.13 (2), p.208-211
Main Authors: Tsui, Gavin Chit, Glenadel, Quentin, Lau, Chan, Lautens, Mark
Format: Article
Language:English
Subjects:
Acetonitriles - chemistry
Boronic Acids - chemistry
Catalysis
Combinatorial Chemistry Techniques
Molecular Structure
Rhodium - chemistry
Stereoisomerism
Sulfones - chemical synthesis
Sulfones - chemistry
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Summary:An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102598p