An intermolecular C–H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines

作者: Christian K. Rank , Alexander W. Jones , Tatjana Wall , Patrick Di Martino-Fumo , Sarah Schröck

DOI: 10.1039/C9CC05240B

关键词: CarbazoleChemistryOxidizing agentIntermolecular forceSimple (abstract algebra)NaphthylamineCombinatorial chemistry

摘要: Highly π-extended hetero-cyclic/aromatic skeletons are of great importance as they can be utilized in many organic material based technologies. Therefore, developing efficient, pre-activation-free, synthetic procedures for the rapid build-up these complex structures remains a high priority objective. The herein presented approach delivers highly fused carbazole from simple naphthylamine derivatives.

参考文章(41)
Stefan Hagen, Henning Hopf, MODERN ROUTES TO EXTENDED AROMATIC COMPOUNDS Topics in Current Chemistry. ,vol. 196, pp. 45- 89 ,(1998) , 10.1007/3-540-69691-1_2
Akimitsu Narita, Xiao-Ye Wang, Xinliang Feng, Klaus Müllen, New advances in nanographene chemistry Chemical Society Reviews. ,vol. 44, pp. 6616- 6643 ,(2015) , 10.1039/C5CS00183H
Sergei I. Kozhushkov, Lutz Ackermann, Ruthenium-catalyzed direct oxidative alkenylation of arenes through twofold C–H bond functionalization Chemical Science. ,vol. 4, pp. 886- 896 ,(2013) , 10.1039/C2SC21524A
Takahiro Ishisone, Satoshi Seo, Yusuke Nonaka, Takuya Kawata, Nobuharu Ohsawa, Highly efficient single-unit white OLED device with emission from both singlet and triplet excitons Journal of The Society for Information Display. ,vol. 22, pp. 404- 411 ,(2014) , 10.1002/JSID.260
D. F. Bowman, B. S. Middleton, K. U. Ingold, Oxidation of amines with peroxy radicals. I. N-phenyl-2-naphthylamine Journal of Organic Chemistry. ,vol. 34, pp. 3456- 3461 ,(1969) , 10.1021/JO01263A053
Morgane Rivoal, Laura Bekere, David Gachet, Vladimir Lokshin, Wladimir Marine, Vladimir Khodorkovsky, Substituted dibenzo[2,3:5,6]-pyrrolizino[1,7-bc]indolo[1,2,3-lm]carbazoles: a series of new electron donors Tetrahedron. ,vol. 69, pp. 3302- 3307 ,(2013) , 10.1016/J.TET.2013.02.007
Alexander W. Jones, Marie-Laure Louillat-Habermeyer, Frederic W. Patureau, Strained Dehydrogenative Ring Closure of Phenylcarbazoles Advanced Synthesis & Catalysis. ,vol. 357, pp. 945- 949 ,(2015) , 10.1002/ADSC.201401136
Helen G. Dunlop, S. Horwood Tucker, 399. Attempts to prepare optically active tervalent nitrogen compounds. Part I. Syntheses of 1 : 9-phenylenecarbazole and derivatives Journal of the Chemical Society (Resumed). pp. 1945- 1956 ,(1939) , 10.1039/JR9390001945
Yoshinori Tominaga, Raymond N. Castle, Photocyclization of aryl‐ and heteroaryl‐2‐propenoic acid derivatives. Synthesis of polycyclic heterocycles Journal of Heterocyclic Chemistry. ,vol. 33, pp. 523- 538 ,(1996) , 10.1002/JHET.5570330302
Marcus D Hanwell, Donald E Curtis, David C Lonie, Tim Vandermeersch, Eva Zurek, Geoffrey R Hutchison, Avogadro: an advanced semantic chemical editor, visualization, and analysis platform Journal of Cheminformatics. ,vol. 4, pp. 17- 17 ,(2012) , 10.1186/1758-2946-4-17