Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds.
We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations.
Division of Chemistry, Department of Biochemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX 75390 (USA).
Hongyin
H
Gao
Qing-Long
QL
Xu
Muhammed
M
Yousufuddin
Daniel H
DH
Ess
László
L
Kürti
D000586:Amination; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011789:Quantum Theory
D006571:Heterocyclic Compounds; D009942:Organometallic Compounds
N-heterocycles; carbazoles; electrophilic amination; nitrobiaryls; regioselectivity