Palladium(II)-catalyzed one-pot syntheses of 9-(pyridin-2-yl)-9H-carbazoles through a tandem C-H activation/C-X (X=C or N) formation process
Chu, JH; Lin, PS; Lee, YM; Shen, WT; Wu, MJ
| HERO ID | 1592487 |
|---|---|
| In Press | No |
| Year | 2011 |
| Title | Palladium(II)-catalyzed one-pot syntheses of 9-(pyridin-2-yl)-9H-carbazoles through a tandem C-H activation/C-X (X=C or N) formation process |
| Authors | Chu, JH; Lin, PS; Lee, YM; Shen, WT; Wu, MJ |
| Journal | Chemistry: A European Journal |
| Volume | 17 |
| Issue | 48 |
| Page Numbers | 13613-13620 |
| Abstract | A new one-pot synthesis of 9-(pyridin-2-yl)-9H-carbazoles through the simultaneous C-H activation and palladium(II)-catalyzed cross-coupling of N-phenylpyridin-2-amines with potassium aryltrifluoroborates is presented. Silver acetate and 1,4-dioxane proved to be the best oxidant and solvent, respectively. The product yields fluctuated from modest to excellent and the reaction showed sufficient functional group tolerance. p-Benzoquinone served as an important ligand for the transmetalation and reductive elimination steps in the catalytic process. The kinetic isotope effects (k(H)/k(D)) for the first and second C-H activation/C-C or C-N formation steps were measured as 2.14 and 1.18, respectively. Finally, a rational catalytic mechanism is presented based on all experimental evidence. |
| Doi | 10.1002/chem.201101528 |
| Pmid | 22025312 |
| Wosid | WOS:000298059600030 |
| Url | https://www.proquest.com/scholarly-journals/palladium-ii-catalyzed-one-pot-syntheses-9/docview/1766616041/se-2?accountid=171501 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Is Peer Review | Yes |
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