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Oxidative ring closure and metal triggered ring opening: syntheses of macrocyclic and linear hexapyrroles

Oxidative ring closure and metal triggered ring opening: syntheses of macrocyclic and linear hexapyrroles

Organic Letters 16(24): 6354-6357

A C6F5-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorin-dipyrrin conjugate (2), and subsequent FeCl3-assisted oxidative cleavage of 2 afforded a terminally di-α-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl3 afforded 3, a hexapyrrinone Fe(3+) complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.

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Accession: 058488828

Download citation: RISBibTeXText

PMID: 25483884

DOI: 10.1021/ol503132r

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