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Iron‐Catalyzed Oxidative C−C and N−N Coupling of Diarylamines and Synthesis of Spiroacridines

2016; Wiley; Volume: 56; Issue: 2 Linguagem: Inglês

10.1002/anie.201610168

1521-3773

Raphael F. Fritsche, Gabriele Theumer, Olga Kataeva, Hans‐Joachim Knölker,

Radical Photochemical Reactions

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 10H-spiro[acridine-9,1'-cyclohexa-2',5'-dien-4'-ones].