Synthesis of Alkylated Aminofluorenes by Palladium-Catalyzed Substitution at Halofluorenes
- 7 January 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (3) , 987-990
- https://doi.org/10.1021/jo035204n
Abstract
New N-substituted 2-amino-9,9-dialkylfluorenes optionally bearing electron-withdrawing substituents such as nitro or cyano in position 7 can be synthesized starting from 2-halo-9,9-dialkylfluorenes by Pd-catalyzed substitution with amines. Chiral amino groups can be introduced by this method too. 2-N,N-Dimethylamino-7-nitro-9H-fluorene was obtained in a convenient way by reductive amination. The N-substituted 2-amino-7-nitro-9H-fluorenes are promising candidates for fluorescence probes for femtosecond solvation dynamics.Keywords
This publication has 17 references indexed in Scilit:
- Palladium-Catalyzed Coupling Reactions of Aryl ChloridesAngewandte Chemie International Edition in English, 2002
- The tenth anniversary of Suzuki polycondensation (SPC)Journal of Polymer Science Part A: Polymer Chemistry, 2001
- Approaches to catalyst discovery. New carbon–heteroatom and carbon–carbon bond formationPure and Applied Chemistry, 1999
- Photoinduced Intramolecular Charge Transfer in a Series of Differently Twisted Donor−Acceptor Biphenyls As Revealed by FluorescenceThe Journal of Physical Chemistry A, 1999
- Rational Development of Practical Catalysts for Aromatic Carbon−Nitrogen Bond FormationAccounts of Chemical Research, 1998
- Palladium-Catalyzed Amination of Aryl Halides: Mechanism and Rational Catalyst DesignSynlett, 1997
- Electronic and second-order nonlinear optical properties of conformationally locked benzylideneanilines and biphenyls. The effect of conformation on the first hyperpolarizabilityJournal of the Chemical Society, Perkin Transactions 2, 1997
- Preneoplastic lesions, DNA adduct formation and mutagenicity of 5-, 7- and 9-hydroxy-2-nitrofluorene, metabolites of the air pollutant 2-nitrofluoreneMutation Research/Genetic Toxicology, 1996
- Aromatic Nucleophilic Substitution of Halobenzenes with Amines under High PressureBulletin of the Chemical Society of Japan, 1991
- Soluble poly(para-phenylene)s. 1. Extension of the Yamamoto synthesis to dibromobenzenes substituted with flexible side chainsPolymer, 1989