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Iftikhar Ali

Synthesis of Substituted 1-Deazapurines via Pd/Cu Catalysed C-H Activation, Substituted Naphthyridines, Quinoxalines, and Trifluoromethyl-Substituted Arenes by Pd(0)-Catalysed Cross-Coupling Reactions

Universität Rostock, 2011

Abstract: The Pd/Cu catalyzed reactions of 3H-imidazo[4,5-b]pyridines (1-deazapurines) via C-H bond activation provided arylated 1-deazapurines. The arylation took place at position 2 of the 1-deazapurines. Pd(0)-catalysed Suzuki-Miyaura cross coupling reactions of 5,7-dichloro-1,6-naphthyridine, 2,6-dichloroquinoxaline and 2,4-dichloro-1-(trifluoromethyl)benzene with different arylboronic acids afforded aryl-substituted naphthyridines, quinoxalines and trifluoromethyl-substituted di- and terphenyls with excellent site-selectivity. The first attack occurred at the more electronically deficient and sterically less hindered position.

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