1352932-75-2Relevant academic research and scientific papers
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, Jean-Ho,Lin, Pi-Shan,Lee, Ya-Ming,Shen, Wei-Ting,Wu, Ming-Jung
, p. 13613 - 13620 (2011/12/22)
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 (kH/kD) 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. Thrown together to perform: A variety of N-pyridylcarbazoles were synthesized through concurrent C-H activation/coupling of N-phenylpyridin-2-amines with potassium aryltrifluoroborates (see scheme; BQ=p-benzoquinone). The catalytic mechanism was elucidated by the examination of X-ray crystal structures of PdII intermediates and key products, as well as control experiments and kinetic isotope effect studies. Copyright
