1,8-bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: synthesis of benzidines via self-coupling of N,N-dialkylanilines

Terunobu Saitoh; Suguru Yoshida; Junji Ichikawa

doi:10.1021/ol048058w

1,8-bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: synthesis of benzidines via self-coupling of N,N-dialkylanilines

Org Lett. 2004 Nov 25;6(24):4563-5. doi: 10.1021/ol048058w.

Authors

Terunobu Saitoh¹, Suguru Yoshida, Junji Ichikawa

Affiliation

¹ Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 15548076
DOI: 10.1021/ol048058w

Abstract

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. [reaction: see text]