Abstract
Jekyll and Hyde: Pinches of LiCl can catalyze orthometalations of halogen-substituted arenes and addition reactions of unsaturated esters, mediated by lithium diisopropylamide. Larger salt portions can transform weak organometallic bases (e.g., Grignard reagents, zincates) into “turbo” reagents of high reactivity and functional group tolerance. But the presence of LiCl, especially as an overlooked metathesis by-product can be detrimental to other catalytic reactions.
| Original language | English |
|---|---|
| Pages (from-to) | 6448-6450 |
| Number of pages | 3 |
| Journal | Angewandte Chemie |
| Volume | 50 |
| Issue number | 29 |
| Early online date | 22 Jun 2011 |
| DOIs | |
| Publication status | Published - 11 Jul 2011 |
Keywords
- amides
- lithium chloride
- metalation
- organolithium
- salt effect
- grignard-reagents
- diisopropylamide
- bases
- catalysis
- autocatalysis
- heteroarenes
- zincation
- arenes
- zinc
- aryl