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Titanium-mediated cross-coupling reactions of 1,3-butadiynes with α-iminonitriles to 3-aminopyrroles: observation of an imino aza-Nazarov cyclization
| Content Provider | Semantic Scholar |
|---|---|
| Author | Sun, Renhong Chen, Haoyi Liu, Yuanhong |
| Copyright Year | 2014 |
| Abstract | Ti(OiPr)4/2 nBuLi-mediated highly efficient cross-coupling reactions of 1,3-butadiynes with α-iminonitriles are described. The method provides convenient access to functionalized 3-aminopyrroles with a wide diversity of substituents in a highly regioselective manner. When optically pure α-iminonitrile is employed in this reaction, a chiral pyrrole derivative is obtained without loss of enantiopurity. Mechanistic study indicates that the 3-aminopyrroles are formed upon treatment of the crude hydrolysis products with silica gel or Lewis acid. A novel imino aza-Nazarov cyclization reaction is proposed to account for the formation of the pyrrole products. Employing the titanium-monoyne complex in this reaction resulted in the homo-coupling of α-iminonitriles, leading to the formation of 1,2-diimines. |
| Starting Page | 940 |
| Ending Page | 946 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/C4QO00159A |
| Volume Number | 1 |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/getauthorversionpdf/C4QO00159A |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/qo/c4/c4qo00159a/c4qo00159a1.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/C4QO00159A |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
