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Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Andreou, Dimitrios Kallitsakis, Michael G. Loukopoulos, Edward Gabriel, Catherine Kostakis, George E. Lykakis, Ioannis N. |
| Copyright Year | 2018 |
| Abstract | The facile copper-catalyzed synthesis of polysubstituted pyrroles from aldehydes, amines, and β-nitroalkenes is reported. Remarkably, the use of α-methyl-substituted aldehydes provides efficient access to a series of tetra- and pentasubstituted pyrroles via an overwhelming 1,2-phenyl/alkyl migration. The present methodology is also accessible to non α-substituted aldehydes, yielding the corresponding trisubstituted pyrroles. On the contrary, the use of ketones, in place of aldehydes, does not promote the organic transformation, signifying the necessity of α-substituted aldehydes. The reaction proceeds under mild catalytic conditions with low catalyst loading (0.3-1 mol %), a broad scope, very good functional-group tolerance, and high yields and can be easily scaled up to more than 3 mmol of product, thus highlighting a useful synthetic application of the present catalytic protocol. Based on formal kinetic studies, a possible radical pathway is proposed that involves the formation of an allylic nitrogen radical intermediate, which in turn reacts with the nitroalkene to yield the desired pyrrole framework via a radical 1,2-phenyl or alkyl migration. |
| Starting Page | 2104 |
| Ending Page | 2113 |
| Page Count | 10 |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/acs.joc.7b03051 |
| PubMed reference number | 29355321 |
| Journal | Medline |
| Volume Number | 83 |
| Issue Number | 4 |
| Alternate Webpage(s) | http://sro.sussex.ac.uk/73055/1/JOC_MS%20pyrrole_rev_220118.pdf |
| Alternate Webpage(s) | http://sro.sussex.ac.uk/id/eprint/73055/1/JOC_MS%20pyrrole_rev_220118.pdf |
| Journal | The Journal of organic chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
