Iron‐Catalyzed Oxidative C−C and N−N Coupling of Diarylamines and Synthesis of Spiroacridines
2016; Wiley; Volume: 129; Issue: 2 Linguagem: Inglês
10.1002/ange.201610168
ISSN1521-3757
AutoresRaphael F. Fritsche, Gabriele Theumer, Olga Kataeva, Hans‐Joachim Knölker,
Tópico(s)Radical Photochemical Reactions
ResumoAbstract We describe iron‐catalyzed intermolecular oxidative coupling reactions of diarylamines to form substituted 2,2′‐bis(arylamino)biaryl compounds, tetraarylhydrazines, and 5,6‐dihydrobenzo[ c ]cinnolines with the same hexadecafluorinated iron–phthalocyanine catalyst. The mild formation of C−C or N−N bonds was controlled by the use of acidic or basic additives. In contrast to most iron‐catalyzed dehydrogenative coupling reactions, ambient air could be used as the sole oxidant. Moreover, iron(III) chloride hexahydrate promoted a one‐pot coupling and subsequent intramolecular dearomative coupling to give 10 H ‐spiro[acridine‐9,1′‐cyclohexa‐2′,5′‐dien‐4′‐ones].
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