18450-12-9Relevant academic research and scientific papers
An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine
Cheng, Hu,Guo, Qiang,Lan, Jingbo,Ran, Chunhao,Wu, Di,Zhang, Huaxing
supporting information, p. 1581 - 1584 (2022/02/10)
Herein, Ag(I)-promoted regioselective intramolecular radical nucleophilic addition/rearrangement of 2-aryl diazaboroles has been accomplished for the first time to construct phenazine structures. This protocol is an umpolung strategy based on the classical electrophilic mechanism, and therefore, a reversed regioselectivity was observed, which provides an opportunity to prepare sterically hindered phenazines. The resulting thermally activated delayed fluorescence (TADF) materials based on phenazine exhibit emission bands from green to red with high quantum yields and moderate fluorescence lifetimes as solid films.
Transition-metal-free tandem oxidative removal of benzylic methylene group by C-C and C-N bond cleavage followed by intramolecular new aryl C-N bond formation under radical conditions
Laha, Joydev K.,Tummalapalli, K. S. Satyanarayana,Gupta, Ankur
supporting information, p. 4392 - 4395 (2015/01/08)
A novel tandem oxidative conversion of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines to phenazines has been achieved under transition-metal-free, mild conditions using K2S2O8 or DDQ as the oxidizing agent. The transformation proceeds through oxidative removal of a benzylic methylene group by C-C and C-N bond cleavage followed by a new aryl C-N bond formation under radical conditions.
Palladium-catalyzed domino double n-arylations (inter- and intramolecular) of 1,2-diamino(hetero)arenes with o,o-dihalo(hetero)arenes for the synthesis of phenazines and pyridoquinoxalines
Laha, Joydev K.,Tummalapalli, K.S. Satyanarayana,Gupta, Ankur
, p. 8330 - 8335 (2014/01/06)
Domino reactions for the synthesis of phenazines have been developed that start from 1,2-diaminoarenes and 1,2-dihaloarenes and proceed through palladium-catalyzed double N-arylations (inter- and intramolecular) followed by an in situ oxidation. A variety of functional groups, which include base-sensitive groups, were well tolerated under the optimized reaction conditions to afford phenazines in good to excellent yields. The protocol was extended to the synthesis of pyridoquinoxalines by employing either o-phenylenediamines and 2,3-dihalopyridines or 1,2-diaminopyridines and 1,2-dihaloarenes. Domino reactions for the synthesis of phenazines have been developed that start from 1,2-diaminoarenes and 1,2-dihaloarenes and proceed through palladium-catalyzed double N-arylations (inter- and intramolecular) followed by an in situ oxidation. The protocol was extended to the synthesis of pyridoquinoxalines. Copyright
Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade
Lian, Yajing,Hummel, Joshua R.,Bergman, Robert G.,Ellman, Jonathan A.
supporting information, p. 12548 - 12551 (2013/09/23)
We report formal [3 + 3] annulations of aromatic azides with aromatic imines and azobenzenes to give acridines and phenazines, respectively. These transformations proceed through a cascade process of Rh(III)-catalyzed amination followed by intramolecular electrophilic aromatic substitution and aromatization. Acridines can be directly prepared from aromatic aldehydes by in situ imine formation using catalytic benzylamine.
