1,8-Bis(diphenylmethylium)naphthalenediyl Dication as an Organic Oxidant:  Synthesis of Benzidines via Self-Coupling of N,N-Dialkylanilines

1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaph...

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Bibliographic Details
Published in:Organic letters 2004-11, Vol.6 (24), p.4563-4565
Main Authors: Saitoh, Terunobu, Yoshida, Suguru, Ichikawa, Junji
Format: Article
Language:English
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Summary:1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048058w