Rhodium-catalyzed Addition of Arylboronic Acids to Nitriles: Application in the Synthesis of Unsymmetrical Polysubstituted Pyridines
Investigations pertaining to the rhodium(I)-catalyzed addition of arylboronic acids to (arylsulfonyl)acetonitriles were undertaken. The resulting carbon-carbon bond forming reaction has led to the efficient synthesis of novel stereoselective (Z)-β-sulfonylvinylamines, which upon acidic hydrolysis, a...
| Main Author: | |
|---|---|
| Other Authors: | |
| Language: | en_ca |
| Published: |
2011
|
| Subjects: | |
| Online Access: | http://hdl.handle.net/1807/31293 |
| Summary: | Investigations pertaining to the rhodium(I)-catalyzed addition of arylboronic acids to (arylsulfonyl)acetonitriles were undertaken. The resulting carbon-carbon bond forming reaction has led to the efficient synthesis of novel stereoselective (Z)-β-sulfonylvinylamines, which upon acidic hydrolysis, afford useful β-keto sulfones possessing a diverse range of aryl and sulfonyl substituents. The synthetic utility of these (Z)-β-sulfonylvinylamines was subsequently explored by generating the corresponding 1-aza-allyl anion equivalents under basic conditions. This interesting anionic intermediate was then introduced to various α,β-unsaturated systems to produce a diverse array of functionalized pyridine derivatives including unsymmetrical polysubstituted pyridines. |
|---|