Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.
W C Peter Tsang, Rachel H Munday, Gordon Brasche, Nan Zheng, Stephen L Buchwald
Index: J. Org. Chem. 73(19) , 7603-10, (2008)
Full Text: HTML
Abstract
The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups. The utility of the new protocol was demonstrated by the concise synthesis of three natural products from commercially available materials.
Related Compounds
Related Articles:
Synthesis of chelating compounds to be used as potential bone seekers.
1966-03-01
[J. Med. Chem. 9(2) , 197-203, (1966)]
Synthesis and molecular structure of 1, 3-dihydro-1-hydroxy-3-methyl-1, 2, 3-benziodoxaphosphole 3-oxide. Balthazor TM, et al.
[J. Org. Chem. 43(23) , 4538-4540, (2978)]
Extension of the Smiles rearrangement. Displacement of an aromatic amide group by an amine nitrogen. Gilman NW, et al.
[J. Org. Chem. 38(2) , 373-377, (1973)]
Palladium-catalyzed direct arylation of pyridine N-oxide with 2-bromoacetanilides. Synthesis of benzisoxazolo [2, 3-a] pyridinium tetrafluoroborates. Myers JT and Hanna JM.
[Tetrahedron Lett. 53(2) , 612-615, (2012)]