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

Iftikhar Ali

doi:10.18453/rosdok_id00001000

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

https://doi.org/10.18453/rosdok_id00001000

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.

doctoral thesis free access

Titel:

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

Beteiligte Personen:

Iftikhar Ali[VerfasserIn]
	1023711575
Peter Langer , Prof. Dr.[AkademischeR BetreuerIn]
Ulrike Lindequist , Prof. Dr.[AkademischeR BetreuerIn]

Beteiligte Körperschaften:

Universität Rostock, Mathematisch-Naturwissenschaftliche Fakultät[Grad-verleihende Institution]
	2147083-2

Zusammenfassung:

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. [English]

Die Pd/Cu-katalysierten Reaktionen von 3H-Imidazo[4,5-b]pyridinen (1-Desazapurinen) via C-H-Aktivierung lieferten arylierte 1-Deazapurine. Die Arylierung fand an Position 2 des 1-Desazapurins statt. Suzuki-Miyaura-Kupplungen von 5,7-Dichlor-1,6-naphthyridin, 2,6-Dichlorchinoxalin und 2,4-Dichlor-1-(trifluormethyl)benzol mit verschiedenen Arylboronsäuren ergab arylsubstituierte Naphthyridine, Chinoxaline, Trifluormethyl-substituierte Biphenyle und Terphenyle mit ausgezeichneter Regioselektivität. Der erste Angriff erfolgte an der elektronisch ärmeren und sterisch weniger gehinderten Position. [German]

Dokumenttyp:

doctoral thesis

Einrichtung:

Faculty of Mathematics and Natural Sciences

Sprache:

English

Sachgruppe der DNB:

540 Chemistry & allied sciences

Veröffentlichung /
Entstehung:

Rostock: Universität Rostock

2011

Identifikatoren: