Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.
β-keto acids and vinyl azides are found to be promising precursors for the synthesis of pyrroles with Mn(acac)3 as a catalyst. One electron oxidation of β-keto acids by Mn(acac)3 induces decarboxylation to afford α-keto radicals, which then add on to vinyl azides, leading to the formation of iminyl...
Saved in:
| Main Author: | |
|---|---|
| Other Authors: | |
| Format: | Final Year Project |
| Language: | English |
| Published: |
2010
|
| Subjects: | |
| Online Access: | http://hdl.handle.net/10356/40466 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | β-keto acids and vinyl azides are found to be promising precursors for the synthesis of pyrroles with Mn(acac)3 as a catalyst. One electron oxidation of β-keto acids by Mn(acac)3 induces decarboxylation to afford α-keto radicals, which then add on to vinyl azides, leading to the formation of iminyl radicals with elimination of dinitrogen. Intramolecular cyclization of the iminyl radical with a carbonyl moiety gives pyrrole after dehydration with regeneration of the Mn(III) complex. |
|---|