Rh(III)-Catalyzed C–H Activation/Intramolecular
Cyclization: Access to N‑Acyl-2,3-dihydro‑1H‑carbazol-4(9H)‑ones from
Cyclic 2‑Diazo-1,3-diketones and N‑Arylamides
posted on 2017-11-30, 16:34authored byYoupeng Zuo, Xinwei He, Yi Ning, Yuhao Wu, Yongjia Shang
A Rh(III)-catalyzed
C–H activation/cyclization cascade reaction
is described. The reaction involves cyclic 2-diazo-1,3-diketones and N-arylamides, and it proceeds via an intermolecular C–C
bond formation and subsequent intramolecular C–N bond formation.
A variety of N-acyl-2,3-dihydro-1H-carbazol-4(9H)-ones were obtained under mild conditions
in good to excellent yields (65–90%). Key features of this
strategy include high-efficiency, operational simplicity, scalability,
and broad functional-group tolerance. In addition, H2O
and N2 are the only byproducts. Carbazole derivatives with
free NH groups can be easily obtained through N-deprotection
reactions.