Synthesis of Functionalized 4-Chlorophthalates, 2-Naphthoates, 2-Fluorobiaryls, and Arylpyridines by Cyclocondensation Reactions of 1,3-Bis(silyloxy)-1,3-butadienes and Related Dienes and by Palladium(0)-Catalyzed Cross-Coupling Reactions

Obaid-ur-Rahman Abid

doi:10.18453/rosdok_id00000693

Obaid-ur-Rahman Abid

Synthesis of Functionalized 4-Chlorophthalates, 2-Naphthoates, 2-Fluorobiaryls, and Arylpyridines by Cyclocondensation Reactions of 1,3-Bis(silyloxy)-1,3-butadienes and Related Dienes and by Palladium(0)-Catalyzed Cross-Coupling Reactions

Universität Rostock, 2010

https://doi.org/10.18453/rosdok_id00000693

Abstract: Fluorinated biaryls and azaxanthones are prepared based on domino reactions of substituted 2-fluoro-1,3-bis(silyloxy)-1,3-butadienes with cyanochromones. Bis(triflate) of 4-chloro-3,5-dihydroxyphthalate used for Suzuki-Miyaura reaction show good site-selectivity controlled by steric parameters. Suzuki-Miyaura and Sonogoshira reactions of the bis(triflate) of phenyl 1,4-dihydroxy-2-naphthoate proceeded with good site-selectivity controlled by electronic parameters. The Diels-Alder reaction of pyridyl- and pyrimidyl-substituted acetylenes with electron-rich dienes yeilded arylpyridines and arylpyrimidines.

Dissertation Freier Zugang

Titel:

Synthesis of Functionalized 4-Chlorophthalates, 2-Naphthoates, 2-Fluorobiaryls, and Arylpyridines by Cyclocondensation Reactions of 1,3-Bis(silyloxy)-1,3-butadienes and Related Dienes and by Palladium(0)-Catalyzed Cross-Coupling Reactions

Beteiligte Personen:

Obaid-ur-Rahman Abid[VerfasserIn]
	141863854
Peter Langer , Prof. Dr.[AkademischeR BetreuerIn]
Torsten Linker , Prof. Dr.[AkademischeR BetreuerIn]

Beteiligte Körperschaften:

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

Zusammenfassung:

Fluorinated biaryls and azaxanthones are prepared based on domino reactions of substituted 2-fluoro-1,3-bis(silyloxy)-1,3-butadienes with cyanochromones. Bis(triflate) of 4-chloro-3,5-dihydroxyphthalate used for Suzuki-Miyaura reaction show good site-selectivity controlled by steric parameters. Suzuki-Miyaura and Sonogoshira reactions of the bis(triflate) of phenyl 1,4-dihydroxy-2-naphthoate proceeded with good site-selectivity controlled by electronic parameters. The Diels-Alder reaction of pyridyl- and pyrimidyl-substituted acetylenes with electron-rich dienes yeilded arylpyridines and arylpyrimidines. [Englisch]

Dokumenttyp:

Dissertation

Einrichtung:

Mathematisch-Naturwissenschaftliche Fakultät

Sprache:

Englisch

Sachgruppe der DNB:

540 Chemie

Veröffentlichung /
Entstehung:

Rostock

Rostock: Universität Rostock

2010