Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 16, Pages 3244-3252Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300652
Keywords
carbanions; CC coupling; mass spectrometry; synthetic methods
Categories
Funding
- University of Ferrara (fondi FAR)
- MIUR (Progetto PRIN) [2009ZSC5K2 004, 20098SJX4F 004]
Ask authors/readers for more resources
The hitherto unreported ability of the methylsulfinyl carbanion (dimsyl anion) to generate acyl anion equivalents is described. The dimsyl anion, in fact, efficiently catalyzes chemoselective intermolecular cross-benzoin condensations of diaryl -diketones (benzils) with various aromatic and aliphatic aldehydes to give the corresponding aryl-aryl and aryl-alkyl benzoin benzoates in an atom-economic fashion. The dimsyl anion acts as an environmentally friendly alternative to the toxic cyanide anion and it is obtained by in situ deprotonation of dimethyl sulfoxide (DMSO) solvent with a catalytic amount of a strong base, potassium tert-butoxide (t-BuOK) the optimal promoter. The assumption that the methylsulfinyl carbanion is the active catalyst in the title transformation is supported by electrospray ionization mass spectrometry (ESI-MS) experiments.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available